Bromotrimethylsilane (HCID 76113)

Names & identifiers

Preferred name: Bromotrimethylsilane
IUPAC: bromo(trimethyl)silane
English name: Bromotrimethylsilane
Molecular formula: C3H9BrSi
Molecular weight: 153.09

Names & synonyms

Bromotrimethylsilane2857-97-8TrimethylbromosilaneTrimethylsilyl bromideSilane, bromotrimethyl-tmsbrJHH5G299BXNSC-139857DTXSID1062671RefChem:121650DTXCID3037838220-672-0

Show more names

(CH3)3SiBrCT2928BromotrimethyL

bromo(trimethyl)silaneTrimethylsilicon bromideTMS bromidetrimethylsilylbromideMFCD00000048bromotrimethyl silaneTMBSC3H9BrSi

Database identifiers

CAS: 2857-97-8
PubChem CID: 76113
DTXSID: DTXSID1062671
UNII: JHH5G299BX
EC Number: 220-672-0
Nikkaji: J150.732J

Properties

Computed structural properties

Topological polar surface area: 0 Å²
Hydrogen bond donors: 0
Hydrogen bond acceptors: 0
Rotatable bonds: 0
Heavy atoms: 5
Formal charge: 0
Complexity: 28.4

Experimental & physicochemical properties

SpringerMaterials Properties29Si nuclear magnetic resonance spectrum

Density1.16 @25 °C

Boiling Point79 °C @760 [mm Hg]

Physicochemical properties

Melting point: -43 °C · -43 °C
Boiling point: 79 °C · 79 °C(lit.)
Density: 1.16 g/mL · 1.16 g/mL at 25 °C(lit.)
refractive index: 20 · n20/D 1.424(lit.)
Flash point: 90 °F · 90 °F
storage temp.: 30 °C · Store below +30°C.
solubility: DECOMPOSES
form: Liquid
Specific Gravity: 1.1725 · 1.1725
color: Clear colorless to yellow
Water Solubility: DECOMPOSES
Sensitive: Moisture Sensitive
Hydrolytic Sensitivity: 8 · 8: reacts rapidly with moisture, water, protic solvents
BRN: 1731135 · 1731135
Stability: Stable. Flammable. Incompatible with strong acids, strong oxidizing agents. May decompose on exposure to water or moist air.
InChI: 1S/C3H9BrSi/c1-5(2,3)4/h1-3H3
InChIKey: IYYIVELXUANFED-UHFFFAOYSA-N
SMILES: C[Si](C)(C)Br
CAS DataBase Reference: 2857 · 2857-97-8(CAS DataBase Reference)
FDA UNII: 5 G299BX · JHH5G299BX
NIST Chemistry Reference: Bromotrimethylsilane(2857-97-8)
EPA Substance Registry System: Silane, bromotrimethyl- (2857-97-8)
UNSPSC Code: 12352103 · 12352103
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS05,GHS07,GHS09
Signal word: Danger
Hazard statements: 225 · H225-H314-H335-H410
Precautionary statements: 210 · P210-P233-P273-P280-P303+P361+P353-P305+P351+P338
target organs: Respiratory system
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
Hazard Codes: C
Risk Statements: 10 · 10-34-29-14
Safety Statements: 16 · 16-26-36/37/39-45-8
RIDADR: 2920 · UN 2920 8/PG 2
WGK Germany: 3 · 3
F: 10 · 10-21
TSCA: TSCA listed
HazardClass: 3 · 3
PackingGroup: II
HS Code: 29310095 · 29310095
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 1 Aquatic · Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3
REACH Registrations: Active
Limited Quantities: 1 L · 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H225 (15.1%): Highly Flammable liquid and vapor [Danger Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P264, P280, P301+P330+P331, P302+P361+P354, P303+P361+P353, P304+P340, P305+P354+P338, P316, P321, P363, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 53 reports by companies from 9 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

Status: Active Update: 23-11-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/24353

Bromotrimethylsilane: Does not have an individual approval but may be used under an appropriate group standard

Hazard Classes and CategoriesFlam. Liq. 2 (15.1%)

Safety & protection

Protective Action Criteria (PAC) · 3 items

1.2 [mg/m3]

13 [mg/m3]

79 [mg/m3]

Safety data

F: 10-21
PPE: Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter
wgk: 3
tsca: TSCA listed
ridadr: UN 2920 8/PG 2
hs_code: 29310095
risk_code: 10-34-29-14
Signal word: Danger
Symbol(GHS): GHS02,GHS05,GHS07,GHS09
hazard_code: C
safety_code: 16-26-36/37/39-45-8
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: II
target organs: Respiratory system
Hazard statements: H225-H314-H335-H410
Limited Quantities: 1.0 L (0.3 gallon) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (500g or 500ml)
REACH Registrations: Active
Hazard Classifications: Aquatic Acute 1Aquatic Chronic 1Eye Dam. 1Flam. Liq. 2Skin Corr. 1BSTOT SE 3
Precautionary statements: P210-P233-P273-P280-P303+P361+P353-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationSilane, bromotrimethyl-: ACTIVE

Applications · 5 items

UsesBromotrimethylsilane can protect or deprotect functional groups selectively, act as silane blocking agent, which is widely used in the syntheses of drugs.

UsesAdefovir intermediate

UsesPowerful silylating agent

UsesBromotrimethylsilane is a mild and selective reagent for cleavage of lactones, epoxides, acetals, phosphonate esters and certain ethers; effective reagent for formation of silyl enol ethers; can function as brominating agent.Amines react with TMS-Br to form isolable adducts, which react readily with ketones to form enamines under mild conditions (eq 15).

General DescriptionBromotrimethylsilane is used with Cl3 to catalyze the direct allylation of a variety of alcohols with allyltrimethylsilane.

Preparation methods · 1 item

Preparationalthough many methods are reported, only a few are provided here: chlorotrimethylsilane undergoes halogen exchange with either magnesium bromide in Et2O or sodium bromide in MeCN, which allows in situ reagent formation (eq 1); alternatively, hexamethyldisilane reacts with bromine in benzene solution or neat, to afford only TMS-Br with no byproducts (eq 2).4 TMS-Br may also be generated by reaction of hexamethyldisiloxane and aluminum bromide (eq 3).However, it should be noted that the reactivity of in situ generated reagent appears to depend upon the method of preparation.