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이소프로필브로마이드

2-Bromopropane

HCID 6358
새 노트새 반응견적 요청하기
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기본 정보개요이름 및 식별자물성안전 및 규제화학 및 산업관련 반응화합물 노트
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기본 정보

CAS
75-26-3
표준 SMILES
CC(C)Br
InChIKey
NAMYKGVDVNBCFQ-UHFFFAOYSA-N
분자식
C3H7Br
평균 분자량
122.99 g/mol
단동위원소 질량
121.97311232

개요

2-Bromopropane (2-BP) can cause cancer according to California Labor Code and the World Health Organization's International Agency for Research on Cancer (IARC). It can cause female reproductive toxicity and male reproductive toxicity according to The National Toxicology Program's Center for the Evaluation of Risks to Human Reproduction.

이름 및 식별자

우선 이름
2-Bromopropane
IUPAC
2-bromopropane
현지명
이소프로필브로마이드
영어명
2-Bromopropane
분자식
C3H7Br
분자량
122.99

이름 및 동의어

2-Bromopropane75-26-3ISOPROPYL BROMIDEPropane, 2-bromo-sec-Propyl bromide2-BROMO-PROPANEUN2344DTXSID7030197R651XOV97ZDTXCID5010197UN-2344RefChem:85898
이름 더 보기
2-브로모프로페인2-브로모프로판이소프로필브롬화물이소프로필브로마이드2-Brompropaniso-C3H7Br2-bromo-propanbromo-2propanepropane,2-bromo-bromo isopropane2-Propyl bromidePropylBromide~98%
200-855-1Isopropylbromide2-bromo propaneMFCD00000147BR1118CCRIS 7919HSDB 6232-Bromopropane, 99%

데이터베이스 식별자

CAS
75-26-3
PubChem CID
6358
DTXSID
DTXSID7030197
ChEMBL
CHEMBL451810
UNII
R651XOV97Z
EC Number
200-855-1
Nikkaji
J1.447H

물성

구조 계산 물성보충 중

XLogP
1.8
극성 표면적
0 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
0
회전 가능 결합 수
0
무거운 원자 수
4
형식 전하
0
복잡도
10.8

실험 및 물리화학적 성질

Chemical ClassesFlammable agents - 3rd degree
SolventsSolvents -> Brominated Solvents
SpringerMaterials PropertiesCoriolis coupling
LogP · 2건

log Kow = 2.14

2.1

Density · 2건

1.31 at 20 °C/4 °C

1.31 @ 20°C

Viscosity1.0012X10-3 Pa.s (liquid) @ -23.15 °C
Color/FormColorless liquid
Solubility · 3건

Miscible with alcohol, benzene, chloroform, ether

SLIGHTLY SOL IN ACETONE

In water, 3,180 mg/L at 20 °C

Flash Point71.6 °F
Endocrine DisruptorsPotential endocrine disrupting compound
Boiling Point · 3건

59-60 °C

138 °F

59.35 °C @760 [mm Hg]

안전 및 규제

안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.

GHS 분류

GHS Classification · 6건

Danger

H225: Highly Flammable liquid and vapor [Danger Flammable liquids]

P203, P210, P233, P240, P241, P242, P243, P260, P280, P303+P361+P353, P318, P319, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

This chemical does not meet GHS hazard criteria for 1.2% (1 of 85) of reports.

Danger

H225 (98.8%): Highly Flammable liquid and vapor [Danger Flammable liquids]

유해성 정보

Regulatory Information · 6건

Chemical: Propane, 2-bromo-

Hazard Traits - Carcinogenicity; Developmental Toxicity; Reproductive Toxicity

Propane, 2-bromo- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propane, 2-bromo- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: No longer Valid Update: 22-07-2010 https://echa.europa.eu/registration-dossier/-/registered-dossier/1580

Propane, 2-bromo-: Does not have an individual approval but may be used under an appropriate group standard

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - Propane, 2-bromo-: Human health tier II assessment
Fire PotentialA very flammable liquid and dangerous fire hazard.
Hazards Summary · 1건

In 1995, an outbreak was reported in Korean electronics workers using 2-BP to degrease switches. Adverse effects were amenorrhea and severe anemia in 17/25 females and oligospermia or azospermia in 6/8 males. The work area concentration was 12.4 ppm, and some workers had skin contact. In a Chinese plant manufacturing 2-BP, 25 workers were studied. Four females exposed at >10 ppm had amenorrhea or polymenorrhea. [ACGIH] See 1-Bromopropane.

화학 및 산업

약리 정보

MeSH Pharmacological Classification · 2건

Chemical agents that increase the rate of genetic mutation by interfering with the function of nucleic acids. A clastogen is a specific mutagen that causes breaks in chromosomes.

Liquids that dissolve other substances (solutes), generally solids, without any change in chemical composition, as, water containing sugar. (Grant & Hackh's Chemical Dictionary, 5th ed)

용도 및 제조

Uses · 4건

Used as a freon substitute; [ChemIDplus] Used in organic synthesis; [Hawley]

Metal Degreasing [Category: Clean]

Used in the synthesis of pharmaceuticals, dyes and other organics

2-Bromopropane is an industrial and laboratory chemical.

U.S. Production · 4건

2023: 50,000 - <250,000 lb

(1994) 10 thousand - 500 thousand pounds

(1998) 10 thousand - 500 thousand pounds

(2002) >500 thousand - 1 million pounds

Industry UsesIntermediate
Methods of ManufacturingObtained by heating isopropyl alcohol with HBr.
General Manufacturing Information · 2건

All Other Basic Inorganic Chemical Manufacturing

Propane, 2-bromo-: ACTIVE

응용 분야 · 2건

개요2-Bromopropane, also known as isopropyl bromide and 2-propyl bromide, is the halogenated hydrocarbon with the formula CH3CHBrCH3. It is a colorless liquid. It is used for introducing the isopropyl functional group in organic synthesis. 2-Bromopropane is prepared by heating isopropanol with hydrobromic acid.

용도2-Bromopropane is a general reagent used to introduce isopropyl group as in the case of the synthesis of various Buchwald ligands. It can also be used as a starting material in the total synthesis of lamellarin D, lamellarin H, ningalin B and (±)-dichroanal. It is sometimes used as an alternative to ozone-depleting cleaning solvents such as chlorofluorocarbons.

관련 반응

1,063건
반응 기록 만들기
HRID 3090 반응식
HRID 3090반응물로uspto-grants-1998_03
HRID 8863 반응식
HRID 8863반응물로uspto-grants-2006_08
HRID 8875 반응식
HRID 8875반응물로uspto-grants-2006_08
HRID 8876 반응식
HRID 8876반응물로uspto-grants-2006_08
HRID 9114 반응식
HRID 9114반응물로uspto-grants-2006_08
HRID 9251 반응식
HRID 9251반응물로uspto-grants-2006_08
HRID 9308 반응식
HRID 9308반응물로uspto-grants-2006_08
HRID 13159 반응식
HRID 13159반응물로uspto-grants-2010_06
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화합물 노트

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새 노트새 반응견적 요청하기
DecompositionWhen heated to decomposition it emits toxic fumes of /hydrogen bromide/.

물리화학적 성질

녹는점
-89 °C · -89 °C (lit.)
끓는 점
59 °C · 59 °C (lit.)
밀도
1.31 g/mL · 1.31 g/mL at 25 °C (lit.)
증기압
224 hPa · 224 hPa (20 °C)
굴절률
20 · n20/D 1.425(lit.)
인화점
67 °F · 67 °F
저장 조건
30 °C · Store below +30°C.
용해도
3.18 g/L · 3.18g/L
물리적 상태
액체
색상
투명한 무색~매우 연한 갈색
폭발한계
4.6 % · 4.6%(V)
수용성
0.3 g/100mL · 0.3g/100mL
Merck
14 · 14,5210
BRN
741852 · 741852
Henry's Law Constant
9 · 9.0×10-4 mol/(m3Pa) at 25℃, Brockbank (2013)
Dielectric constant
9.46 · 9.4600000000000009
안정성
안정적인. 가연성. 강한 산화제와 호환되지 않습니다.
InChI
1S/C3H7Br/c1-3(2)4/h3H,1-2H3
InChIKey
NAMYKGVDVNBCFQ-UHFFFAOYSA-N
SMILES
CC(C)Br
NIST
2 · Propane, 2-bromo-(75-26-3)
EPA
2 · Propane, 2-bromo- (75-26-3)

화학적 성질

colourless liquid

DOT Emergency Guidelines · 5건

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Fire or Explosion: HIGHLY FLAMMABLE: Will be easily ignited by heat, sparks or flames. Vapors may form explosive mixtures with air. Vapors may travel to source of ignition and flash back. Most vapors are heavier than air. They will spread along ground and collect in low or confined areas (sewers, basements, tanks). Vapor explosion hazard indoors, outdoors or in sewers. Those substances designated with a (P) may polymerize explosively when heated or involved in a fire. Runoff to sewer may create fire or explosion hazard. Containers may explode when heated. Many liquids are lighter than water.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Health: May cause toxic effects if inhaled or absorbed through skin. Inhalation or contact with material may irritate or burn skin and eyes. Fire will produce irritating, corrosive and/or toxic gases. Vapors may cause dizziness or suffocation. Runoff from fire control or dilution water may cause pollution.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Public Safety: CALL Emergency Response Telephone Number on Shipping Paper first. If Shipping Paper not available or no answer, refer to appropriate telephone number listed on the inside back cover. As an immediate precautionary measure, isolate spill or leak area for at least 50 meters (150 feet) in all directions. Keep unauthorized personnel away. Stay upwind. Keep out of low areas. Ventilate closed spaces before entering.

/GUIDE 129: FLAMMABLE LIQUIDS (Polar/Water-Miscible/Noxious)/ Protective Clothing: Wear positive pressure self-contained breathing apparatus (SCBA). Structural firefighters' protective clothing will only provide limited protection.

For more DOT Emergency Guidelines (Complete) data for 2-BROMOPROPANE (8 total), please visit the HSDB record page.

Hazard Classes and Categories · 6건

Flam. Liq. 2 (98.8%)

Flammable liquid - category 2

Flammable liquids - Category 2

Flammable liquids - Category 2

Flammable liquids - Category 2

Flammable agents - 3rd degree

Shipment Methods and Regulations · 3건

No person may /transport,/ offer or accept a hazardous material for transportation in commerce unless that person is registered in conformance ... and the hazardous material is properly classed, described, packaged, marked, labeled, and in condition for shipment as required or authorized by ... /the hazardous materials regulations (49 CFR 171-177)./

The International Air Transport Association (IATA) Dangerous Goods Regulations are published by the IATA Dangerous Goods Board pursuant to IATA Resolutions 618 and 619 and constitute a manual of industry carrier regulations to be followed by all IATA Member airlines when transporting hazardous materials.

The International Maritime Dangerous Goods Code lays down basic principles for transporting hazardous chemicals. Detailed recommendations for individual substances and a number of recommendations for good practice are included in the classes dealing with such substances. A general index of technical names has also been compiled. This index should always be consulted when attempting to locate the appropriate procedures to be used when shipping any substance or article.

Shipping Name/ Number DOT/UN/NA/IMO · 2건

UN 2344; Bromopropanes

IMO 3.2; Bromopropanes

안전 및 보호

Fire Fighting Procedures · 1건

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. /Bromopropanes/

Storage Conditions · 1건

...Materials which are toxic as stored or which can decompose into toxic components...should be stored in a cool, well ventilated place, out of the direct rays of the sun, away from areas of high fire hazard, and should be periodically inspected. Incompatible materials should be isolated...

Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 2건

If material on fire or involved in fire: Do not extinguish fire unless flow can be stopped. Use water in flooding quantities as fog. Solid streams of water may be ineffective. Cool all affected containers with flooding quantities of water. Use alcohol foam, dry chemical or carbon dioxide. Keep run-off water out of sewers and water sources. /Bromopropanes/

Personnel protection: Avoid breathing vapors. Keep upwind. Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing. /Bromopropanes/

Protective Action Criteria (PAC) · 3건

3.0 [ppm]

230 [ppm]

1400 [ppm]

Personal Protective Equipment (PPE)Personnel Protection: ... Wear appropriate chemical protective gloves, boots and goggles. /Bromopropanes/

독성 정보

Treatment · 1건

EYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.

Health Effects · 1건

2-Bromopropane is a strong lachrymator. Chronic exposure has been shown to have teratogenic effects in mouse and rat embryos. Very high chronic doses led to developmental toxicity which included an increase in the fetal deaths, a decrease in the litter size, and a reduction in the fetal body weight. In addition, an increase in the incidence of fetal external, visceral, and skeletal abnormalities was seen. Chronic exposure to 2-bromopropane depletes spermatogenic cells in male rats and oocytes in female rats. Humans exposed to 2-bromopropane exhibited oligospermia, amenorrhea and other reproductive toxic effects.

Environmental Fate · 3건

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow of 2.14(2) and a regression derived equation(3), indicates that isopropyl bromide is expected to have moderate mobility in soil(SRC). Volatilization of isopropyl bromide from moist soil surfaces is expected to be an important fate process(SRC) given an estimated Henry's Law constant of 0.011 atm-cu m/mole(SRC) derived from its extrapolated vapor pressure of 216 mm Hg(4) and water solubility of 3180 mg/L(5). The potential for volatilization of isopropyl bromide from dry soil surfaces exists(SRC) based upon its extrapolated vapor pressure(4). No terrestrial biodegradation data were located for isopropyl bromide(SRC, 2005); however, an aqueous aerobic screening study using an activated sludge inoculum indicated that this compound is readily biodegradable(6).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 350(SRC), determined from a measured log Kow of 2.14(2) and a regression derived equation(3), indicates that isopropyl bromide is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is expected(3) based upon an estimated Henry's Law constant of 0.011 atm-cu m/mole(SRC), derived from an extrapolated vapor pressure of 216 mm Hg(4) and water solubility of 3180 mg/L(5). Using this Henry's Law constant and an estimation method(3), volatilization half-lives for a model river and model lake are 1 hour and 4 days, respectively(SRC). According to a classification scheme(6), an estimated BCF of 9(SRC), from a log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). The hydrolysis half-life of isopropyl bromide was reported as 2.1 days at 25 °C(8). No aquatic biodegradation data were located for isopropyl bromide(SRC, 2005); however, an aqueous aerobic screening study using an activated sludge inoculum indicated that this compound is readily biodegradable(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), isopropyl bromide, which has an extrapolated vapor pressure of 216 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase isopropyl bromide is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 18 days(SRC), calculated from its rate constant of 8.8X10-13 cu cm/molecule-sec at 25 °C(3).

Adverse EffectsNeurotoxin - Acute solvent syndrome
Exposure RoutesOral (L626) ; inhalation (L626) ; dermal (L626)
Toxicity Summary · 1건

Organobromide compounds, especially alkylbromides are strong alkylating agents. Consequently they can randomly modify the surfaces of proteins and lipids, leading to the disruption of enzyme, transporter or membrane functions. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. Alkylation of DNA by alkylbromides may also lead to mutations. 2-bromopropane triggers the mitochondrion-dependent apoptotic pathway via ROS (reactive oxygen species) generation. 2-bromopropane has also been shown to induce DNA damage, impair functional antioxidant cellular defenses, and enhance the lipid peroxidation in cultured Leydig cells.

Signs and Symptoms · 1건

May cause skin, eye and respiratory tract irritation. May affect behavior/central nervous system (central nervous system depression, excitement fatigue, headache, dizziness, stupor,unconsciousness and possible coma). If ingested, 2-bromopropane may cause gastrointestinal tract irritation with nausea, and vomiting. It may also affect behavior/central nervous system with symptoms similar to those for inhalation. May also cause kidney damage and liver damage.

Soil Adsorption/Mobility · 1건

The Koc of isopropyl bromide is estimated as 350(SRC), using a measured log Kow of 2.14(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that isopropyl bromide is expected to have moderate mobility in soil(SRC).

Human Toxicity Excerpts · 3건

/HUMAN EXPOSURE STUDIES/ An outbreak of reproductive and hematopoietic toxicities occurred in Korean electronics workers in 1995 exposed to solvents containing 2-BP that were used as alternatives to chlorofluorocarbons for cleaning tactile switches. Seventeen of 25 female workers showed ovarian dysfunction accompanied by amenorrhea and severe anemia, and 6 of 8 male workers had oligospermia or azospermia. The mean ambient 2-BP concentration in the work area was 12.4 ppm, and the 2-BP concentration inside the hood of the cleaning baths was 4141 ppm. Some workers had skin contact with 2-BP. Two of the affected female workers regained normal ovarian function within 2 years following exposure.

/HUMAN EXPOSURE STUDIES/ Sixteen Korean female laborers who had been exposed to a cleaning solvent composed mainly of 2-bromopropane developed primary ovarian failure. Histologic findings from these patients' ovaries were similar to those observed in ovarian failure caused by radiation or chemotherapy, i.e., reduced number and developmental arrest of primary follicles, interstitial fibrosis and hyalinization of blood vessels. We followed their clinical course for 2 years and found that two patients recovered normal ovarian function spontaneously: one became pregnant and delivered a normal full-term baby, and the other resumed regular menstrual periods with normal hormonal values. Our observations support the idea that the increasing prevalence of ovarian failure in recent years might be due to an increase in presently unidentified environmental toxic agents.

/HUMAN EXPOSURE STUDIES/ A study of 25 workers in a Chinese 2-BP manufacturing plant found amenorrhea or polymenorrhea in 4 female workers exposed at >10 ppm (TWA) 2-BP.

Artificial Pollution SourcesIsopropyl bromide's production and use in the synthesis of pharmaceuticals, dyes, and other organics(1) may result in its release to the environment through various waste streams(SRC).
Environmental Biodegradation · 1건

Isopropyl bromide present at 100 mg/L, reached 73-89% of its theoretical BOD in 2 weeks using an activated sludge inoculum at 30 mg/L and the Japanese MITI test(1). Half-lives for the biodehalogenation of isopropyl bromide are 35 (oxygen insertion), 279 (substitution), and 40 hours (substitution) by the bacterial strains Pseudomonas putida, Pseudomonas sp., and Flavobacterium sp., respectively(2).

Carcinogen Classification · 6건

2-Bromopropane

Group 2A: Probably carcinogenic to humans

Volume 133: (2024) Anthracene, 2-Bromopropane, Butyl Methacrylate, and Dimethyl Hydrogen Phosphite

2024 online

2023

No indication of carcinogenicity to humans (not listed by IARC).

안전 데이터

wgk
1
tsca
TSCA listed
rtecs
TX4111000
ridadr
UN 2344 3/PG 2
HS 번호
29033036
risk_code
60-11-48/20-66
hazard_code
F,T
safety_code
53-16-45
포장분류
II
위험 등급
3
기존화학 물질
KE-03708
Hazard Classifications
Flam. Liq. 2Repr. 1ASTOT RE 2 Inhalation
스토리지 클래스
3 - Flammable liquids
유해 물질 데이터
75-26-3(Hazardous Substances Data)

제조 방법

2-Bromopropane is commercially available. It may be prepared in the ordinary manner of alkyl bromides, by reacting isopropanol with phosphorus and bromine, or with phosphorus tribromide.

상·하류 제품 정보

상류 원료

브롬화수소Concentrated sulfuric acid이소프로필알코올탄산나트륨(경회)

하류 제품

7-이소프로폭시-3-페닐-4H-1-벤조피란-4-원2-ISOPROPOXYPHENYLBORONIC ACID프로폭서7-이소프로폭시-3-페닐-4H-1-벤조피란-4-원5-클로로-2-(3,4-디메톡시페닐)-2-이소프로필발레로니트릴2-(4-CHLOROPHENYL)-3-METHYLBUTYRONITRILE2-Bromo-3-methylbutyric acid2-(4-Chlorophenyl)-3-methylbutyric acid2,4,6-트리아이소프로필벤젠설포닐 염화물메틸(3-)-2-부탄올Verapamil2- 디 -t- 부틸 포스 피노 -2 ', 4', 6'- 트리 -i- 프로필 -1,1'- 비 페닐ISOPROPYLDIPHENYLPHOSPHINE아이소프로폭시에탄올메프로닐아닐로포스VALERATE트리이소프로필벤젠-1,3,5펜발러레이트이사조포스1,5-dichloro-2-(1-methylethoxy)-4-nitrobenzene4-이소프록폭시벤조산3-메틸-2-(3,4-디메톡시페닐)부티로니트릴2-Isopropoxyphenol