降冰片烯

  • 基本信息
  • 制备方法及用途
  • 物化性质
  • 安全信息
  • 毒理性
  • MSDS
  • 结构与计算化学
  • 上游产品
  • 下游产品
  • 表征图谱

降冰片烯 基本信息

中文名称:
降冰片烯 
中文别名:
降冰片烯;
降莰烯;
双环[2.2.1]庚-2-烯;
甲[0XA29C]烯 
英文名称:
Bicyclo[2.2.1]hept-2-ene
英文别名:
norbornene;
2-NORBORNENE;
Bicyclo[2.2.1]hept-2-ene;
bicyclo[2.2.1]hept-2-ene;
bicyclo(2,2,1)hept-2Z-ene;
norborn-2-ene;
bicyclo(2.2.1)heptene;
3,6-Endomethylenecyclohexene;
Norbornylene,stabilized;
Norcamphene;
bicyclo[2.2.1]hept-5-ene;
2-Norbornylene;
2-Norbornene;
Norbornene;
Norbornylene;
Norfenchene 
CAS No.:
498-66-8
分 子 式:
C7H10
分 子 量:
94.15
精确分子量:
94.07830
PSA:
0.00000
MDL:
MFCD00082304
EINECS:
207-866-0
BRN:
1098544
InChI:
InChI=1/C7H10/c1-2-7-4-3-6(1)5-7/h1-2,6-7H,3-5H2/t6-,7+
危险品标志:
F:Highly flammable
风险术语:
R11;
安全术语:
S16; S33; S9;
分子结构式:
SDS:
查看

降冰片烯 制备方法及用途

制备方法

1.制法: 2-莰酮对甲苯磺酰腙(4):于装有回流冷凝器的反应瓶中,加入对甲苯磺酰肼(3)44g(0.24mol),樟脑(2)31.6(0.2mol)和300mL95%的乙醇,1mL浓盐酸,加热回流反应2h。冰浴冷却,抽滤析出的结晶,空气中干燥。用乙醇重结晶,得无色针状结晶2-莰酮对甲苯磺酰腙(4)50g,mp163~164℃,收率73%。2-莰烯(1):于装有搅拌器、温度计、滴液漏斗、回流冷凝器(安氯化钙干燥管)的反应瓶中,加入上述化合物(4)32g(0.1mol),干燥的乙醚450mL,水浴冷却,搅拌下慢慢滴加150mL1.6mol/L的甲基锂的乙醚溶液(0.24mol),约1h加完。反应中沉淀出对甲苯亚磺酸锂,同时反应液变为深橙红色。小心地加入少量的水以使甲基锂分解,而后加水200mL。分出有机层,水洗四次。水层合并后用乙醚提取两次。合并乙醚层,无水硫酸钠干燥。分馏蒸出乙醚至剩余50~60mL,加入100mL新蒸馏的戊烷,蒸馏至30~50mL,再加入戊烷,蒸馏至30~40mL。过中性氧化铝色谱柱,用戊烷洗脱。分馏浓缩蒸出溶剂戊烷,将剩余物转入50mL烧瓶中,借助于油浴和红外灯通过U型管进行蒸馏。分出前馏分(戊烷和2-莰烯)后,在冷却的接受瓶中得到无色结晶2-莰烯①(1)8.5~8.8g,mp110~111℃,收率63%~65%。注:①利用该方法可以由酮制备烯类化合物。由2-甲基环己酮的对甲苯磺酰腙可以制备-3-甲基环己烯,气相色谱分析表明收率为98%。2.于装有搅拌器、回流冷凝器(装氯化钙干燥管)、滴液漏斗的反应瓶中,加入无水乙醇600mL,分批加入切碎的金属钠46g(2.0mol),当钠全部反应完后,滴加丙二酸二乙酯(2)160g(1.0mol)。加完后于65℃滴加烯丙基溴(3)254g(2.1mol),约3~4h加完。反应中析出溴化钠沉淀,用酚酞试纸检验反应是否完全。当反应液与酚酞试纸不变色时,搅拌下回流1h。蒸出约400mL乙醇,冷却后加入450mL水。分出有机层,水层用苯提取三次。合并有机层,无水硫酸钠干燥,蒸出苯后,减压分馏,收集122~124℃/0.94kPa的馏分,得二烯丙基丙二酸二乙酯(1)195~214g,收率82%~87%。

合成制备方法

1.制法:

2-莰酮对甲苯磺酰腙(4):于装有回流冷凝器的反应瓶中,加入对甲苯磺酰肼(3)44g(0.24mol),樟脑(2)31.6(0.2mol)和300mL95%的乙醇,1mL浓盐酸,加热回流反应2h。冰浴冷却,抽滤析出的结晶,空气中干燥。用乙醇重结晶,得无色针状结晶2-莰酮对甲苯磺酰腙(4)50g,mp163~164℃,收率73%。2-莰烯(1):于装有搅拌器、温度计、滴液漏斗、回流冷凝器(安氯化钙干燥管)的反应瓶中,加入上述化合物(4)32g(0.1mol),干燥的乙醚450mL,水浴冷却,搅拌下慢慢滴加150mL1.6mol/L的甲基锂的乙醚溶液(0.24mol),约1h加完。反应中沉淀出对甲苯亚磺酸锂,同时反应液变为深橙红色。小心地加入少量的水以使甲基锂分解,而后加水200mL。分出有机层,水洗四次。水层合并后用乙醚提取两次。合并乙醚层,无水硫酸钠干燥。分馏蒸出乙醚至剩余50~60mL,加入100mL新蒸馏的戊烷,蒸馏至30~50mL,再加入戊烷,蒸馏至30~40mL。过中性氧化铝色谱柱,用戊烷洗脱。分馏浓缩蒸出溶剂戊烷,将剩余物转入50mL烧瓶中,借助于油浴和红外灯通过U型管进行蒸馏。分出前馏分(戊烷和2-莰烯)后,在冷却的接受瓶中得到无色结晶2-莰烯(1)8.5~8.8g,mp110~111℃,收率63%~65%。注:①利用该方法可以由酮制备烯类化合物。由2-甲基环己酮的对甲苯磺酰腙可以制备-3-甲基环己烯,气相色谱分析表明收率为98%。[1]

2.于装有搅拌器、回流冷凝器(装氯化钙干燥管)、滴液漏斗的反应瓶中,加入无水乙醇600mL,分批加入切碎的金属钠46g(2.0mol),当钠全部反应完后,滴加丙二酸二乙酯(2)160g(1.0mol)。加完后于65℃滴加烯丙基溴(3)254g(2.1mol),约3~4h加完。反应中析出溴化钠沉淀,用酚酞试纸检验反应是否完全。当反应液与酚酞试纸不变色时,搅拌下回流1h。蒸出约400mL乙醇,冷却后加入450mL水。分出有机层,水层用苯提取三次。合并有机层,无水硫酸钠干燥,蒸出苯后,减压分馏,收集122~124℃/0.94kPa的馏分,得二烯丙基丙二酸二乙酯(1)195~214g,收率82%~87%。[2]

用途简介

生化试剂。

用途

生化试剂。

降冰片烯 物化性质

密度:
0.955 g/cm3
熔点:
44-46 °C(lit.)
沸点:
96 °C(lit.)
闪点:
5 °F
折射率:
1.52
蒸汽压:
50.685mmHg at 25°C
存储条件/存储方法:

本品应远离火种于通风良好处密封保存。

稳定性相关:

按规格使用和贮存,不会发生分解,避免与氧化物接触。

其它信息:

1. 性状:无色结晶。高度易燃。

2. 熔点(℃):44~46

3. 沸点(℃):96

4. 闪点(℃):-15

5. 溶解性:不溶于水。

降冰片烯 安全信息

包装等级:
II
风险类别:
4.1
WGK_Germany:
1
德国有关水污染物质的分类清单
危险类别码:
R11
安全说明:
S9-S16-S29-S33
RTECS号:
RB7900000
安全标志:
S9:保持容器在一个有良好通风放的场所。
S16:远离火源。
S29:不要将残余物倾入排水口。
S33:采取防护措施防止静电发生。
危险标志:
F:Highlyflammable;

降冰片烯 毒理性

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RB7900000
CHEMICAL NAME :
2-Norbornene
CAS REGISTRY NUMBER :
498-66-8
LAST UPDATED :
199709
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C7-H10
MOLECULAR WEIGHT :
94.17
WISWESSER LINE NOTATION :
L55 A CUTJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
11300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIHAAP American Industrial Hygiene Association Journal. (AIHA, 475 Wolf Ledges Pkwy., Akron, OH 44311) V.19- 1958- Volume(issue)/page/year: 30,470,1969
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>5 mL/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
AIHAAP American Industrial Hygiene Association Journal. (AIHA, 475 Wolf Ledges Pkwy., Akron, OH 44311) V.19- 1958- Volume(issue)/page/year: 30,470,1969 *** OCCUPATIONAL EXPOSURE LIMITS *** OEL-RUSSIA:STEL 3 mg/m3 JAN 1993
毒理学数据:

1、急性毒性:大鼠经口LD50:11300mg/kg,除致死剂量外无详细说明;

兔子经皮肤LD50:>5 mL/kg,除致死剂量外无详细说明;

半数致死量(大鼠,口服)11.3g/kg。

生态数据:

该物质对环境可能有危害,对水体应给予特别注意。

降冰片烯 MSDS

Name: Norbornylene stabilized 99% Material Safety Data Sheet
Synonym: Bicyclo[2.2.1]-2-heptene; Norbornene; Norbornylene; Bicyclo[2.2.1]hept-2-ene
CAS: 498-66-8
Section 1 - Chemical Product   MSDS Name:Norbornylene stabilized 99% Material Safety Data Sheet
Synonym:Bicyclo[2.2.1]-2-heptene; Norbornene; Norbornylene; Bicyclo[2.2.1]hept-2-ene

Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS
CAS# Chemical Name content EINECS#
498-66-8 Norbornylene 99 207-866-0
Hazard Symbols: F
Risk Phrases: 11

Section 3 - HAZARDS IDENTIFICATION
  EMERGENCY OVERVIEW
Highly flammable.Extremely flammable.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract.
Inhalation:
May cause respiratory tract irritation. May be harmful if inhaled.
Chronic:
No information found.

Section 4 - FIRST AID MEASURES
  Eyes: In case of contact, immediately flush eyes with plenty of water for at least 15 minutes. Get medical aid.
Skin:
In case of contact, flush skin with plenty of water. Remove contaminated clothing and shoes. Get medical aid if irritation develops and persists. Wash clothing before reuse.
Ingestion:
If swallowed, do not induce vomiting unless directed to do so by medical personnel. Never give anything by mouth to an unconscious person. Get medical aid.
Inhalation:
If inhaled, remove to fresh air. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:
Treat symptomatically and supportively.

Section 5 - FIRE FIGHTING MEASURES
  General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. Vapors can travel to a source of ignition and flash back. Flammable solid.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or chemical foam.

Section 6 - ACCIDENTAL RELEASE MEASURES
  General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Vacuum or sweep up material and place into a suitable disposal container. Remove all sources of ignition. Provide ventilation. Use only non-sparking tools and equipment.

Section 7 - HANDLING and STORAGE
  Handling:
Use spark-proof tools and explosion proof equipment. Avoid breathing dust, vapor, mist, or gas. Avoid contact with eyes, skin, and clothing. Take precautionary measures against static discharges. Use only with adequate ventilation. Keep away from heat, sparks and flame.
Storage:
Keep away from sources of ignition. Store in a tightly closed container. Refrigerator/flammables.

Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
  Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 498-66-8: Russia: 3 mg/m3 TWA Personal Protective Equipment Eyes: Wear chemical splash goggles.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear a chemical apron.
Respirators:
Follow the OSHA respirator regulations found in 29 CFR 1910.134 or European Standard EN 149. Use a NIOSH/MSHA or European Standard EN 149 approved respirator if exposure limits are exceeded or if irritation or other symptoms are experienced.

Section 9 - PHYSICAL AND CHEMICAL PROPERTIES
 
Physical State: Solid
Color: white
Odor: pungent sour
pH: Not available.
Vapor Pressure: 39.2 mm Hg @ 25 deg C
Viscosity: Not available.
Boiling Point: 96 deg C @ 760 mm Hg
Freezing/Melting Point: 42 - 46 deg C
Autoignition Temperature: Not available.
Flash Point: -15 deg C ( 5.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature:
Solubility in water: practically insoluble
Specific Gravity/Density:
Molecular Formula: C7H10
Molecular Weight: 94.15

Section 10 - STABILITY AND REACTIVITY
  Chemical Stability:
No information found.
Conditions to Avoid:
High temperatures, ignition sources, confined spaces.
Incompatibilities with Other Materials:
Strong oxidizing agents, strong acids.
Hazardous Decomposition Products:
Carbon monoxide, carbon dioxide.
Hazardous Polymerization: May occur.

Section 11 - TOXICOLOGICAL INFORMATION
  RTECS#:
CAS# 498-66-8: RB7900000 LD50/LC50:
CAS# 498-66-8: Oral, mouse: LD50 = 13000 mg/kg; Oral, rat: LD50 = 11300 mg/kg; Skin, rabbit: LD50 = >5 mL/kg.
Carcinogenicity:
Norbornylene - Not listed by ACGIH, IARC, or NTP.
Other:
See actual entry in RTECS for complete information.

Section 12 - ECOLOGICAL INFORMATION
 

Section 13 - DISPOSAL CONSIDERATIONS
  Dispose of in a manner consistent with federal, state, and local regulations.

Section 14 - TRANSPORT INFORMATION
 
IATA
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.*
Hazard Class: 4.1
UN Number: 1325
Packing Group: II
IMO
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing Group: II
RID/ADR
Shipping Name: FLAMMABLE SOLID, ORGANIC, N.O.S.
Hazard Class: 4.1
UN Number: 1325
Packing group: II

Section 15 - REGULATORY INFORMATION
 
European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: F
Risk Phrases:
R 11 Highly flammable.
Safety Phrases:
S 9 Keep container in a well-ventilated place.
S 16 Keep away from sources of ignition - No
smoking.
S 33 Take precautionary measures against static
discharges.
WGK (Water Danger/Protection)
CAS# 498-66-8: No information available.
Canada
CAS# 498-66-8 is listed on Canada's NDSL List.
CAS# 498-66-8 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 498-66-8 is listed on the TSCA inventory.


SECTION 16 - ADDITIONAL INFORMATION
N/A

降冰片烯 分子结构与计算化学数据

分子结构数据

1、   摩尔折射率:29.93

2、   摩尔体积(cm3/mol):98.5

3、   等张比容(90.2K):240.3

4、   表面张力(dyne/cm):35.4

5、   极化率(10-24cm3):11.86

计算化学数据

1.疏水参数计算参考值(XlogP):2.4

2.氢键供体数量:0

3.氢键受体数量:0

4.可旋转化学键数量:0

5.互变异构体数量:无

6.拓扑分子极性表面积0

7.重原子数量:7

8.表面电荷:0

9.复杂度:90.6

10.同位素原子数量:0

11.确定原子立构中心数量:0

12.不确定原子立构中心数量:2

13.确定化学键立构中心数量:0

14.不确定化学键立构中心数量:0

15.共价键单元数量:1

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