630-17-1

Basic information

• Product Name: 1-BROMO-2,2-DIMETHYLPROPANE
• Synonyms: NEOPENTYL BROMIDE;1-BROMO-2,2-DIMETHYLPROPANE;2,2-DIMETHYL-1-BROMOPROPANE;(CH3)3CCH2Br;1-bromo-2,2-dimethyl-propan;propane,1-bromo-2,2-dimethyl-;Neopentylbromide,98%;Neopentyl broMide, 98% 5GR
• CAS NO: 630-17-1
• Molecular Formula: C₅H₁₁Br
• Molecular Weight: 151.04
• EINECS: 211-132-5
• Mol File: 630-17-1.mol
• Article Data: 21

Chemical Properties

• Melting Point: -105.4°C (estimate)
• Boiling Point: 105-106 °C767 mm Hg(lit.)
• Flash Point: 44 °F
• Appearance: colourless liquid
• Density: 1.199 g/mL at 25 °C(lit.)
• Vapor Pressure: 31mmHg at 25°C
• Refractive Index: n20/D 1.436(lit.)
• Storage Temp.: 2-8°C
• Water Solubility: Soluble in ethanol, ether, aetone and benzene. Insoluble in water.
• Stability: Stable. Highly flammable. Incompatible with strong oxidizing agents, strong bases.
• BRN: 1730989
• CAS DataBase Reference: 1-BROMO-2,2-DIMETHYLPROPANE(CAS DataBase Reference)
• NIST Chemistry Reference: 1-BROMO-2,2-DIMETHYLPROPANE(630-17-1)
• EPA Substance Registry System: 1-BROMO-2,2-DIMETHYLPROPANE(630-17-1)

Safety Data

• Hazard Codes: F,Xi
• Statements: 11-36/37/38
• Safety Statements: 26
• RIDADR: UN 1993 3/PG 2
• WGK Germany: 3
• TSCA: Yes
• HazardClass: 3
• PackingGroup: II
• Hazardous Substances Data: 630-17-1(Hazardous Substances Data)

Usage

Chemical Properties

colourless liquid

Uses

Neopentyl bromide is used in synthesis of S-alkylated cysteine derivatives with branched alkyl chains. It can be used in agrochemical, pharmaceutical and dyestuff field .

InChI:InChI=1/C5H11Br/c1-5(2,3)4-6/h4H2,1-3H3

Synthetic route

dineopentyl(bis(triphenylphosphine))palladium(II) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With bromine In toluene	89%

1-(2,2-dimethyl-propyl)-2,4-diphenyl-5,6-dihydro-benzo[h]quinolinium; bromide (87444-95-9) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
at 200 - 220℃; under 0.3 - 0.8 Torr;	87%

dineopentyl(bis(triphenylphosphine))nickel(II) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With bromine inert atmosphere; GLC;	87%

thallium(I) 3,3-dimethylbutanoate → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With bromine In tetrachloromethane 0 deg C, 1 h, 20 deg C, 1 h, reflux, 1 h;	82%

2,2-dimethylpropane (463-82-1) → 3,3-dimethylpyrrolidine-2,5-dione (3437-29-4) + bromodichloromethane (75-27-4) + 2,2-dimethylpropyl bromide (630-17-1) + 3-bromo-3-methylbutanoyl isocyanate (82621-87-2)

Conditions	Yield
With ethene; dichloromethane; 22DMNBS; bromine at 12℃; for 30h; Irradiation; Further byproducts given. Yields of byproduct given;	A 67.7% B 32.3% C 45.2% D n/a

2,2-dimethyl-propanol-1 (75-84-3) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With hydrogen bromide; Aliquat 336 In chlorobenzene at 85℃;	30%
With quinoline; phosphorus tribromide
With pyridine; hydrogen fluoride; ammonium bromide

2-(2,2-Dimethyl-propoxy)-1,3-diphenyl-[1,3,2]diazaphospholidine (85558-04-9) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With bromine In dichloromethane at 0℃;	30%

diazomethane (186581-53-3, 908094-01-9) + t-butyl bromide (507-19-7) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With nitrogen Irradiation.UV-Licht;

methylene (2465-56-7) + t-butyl bromide (507-19-7) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
aus Diazomethan durch Photolyse hergestellt;

2,2-dimethylpropane (463-82-1) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With N-Bromosuccinimide at 15℃; Irradiation; competitive brominaton reactions with CH2Cl2; further brominating system (NBS-DCE; NBS-Br2);
With bromine at 50℃; Product distribution; competitive brominaton reaction with CH2Cl2; relative reactivities per hydrogen have been determined;
With N-Bromosuccinimide at 15℃; Irradiation; competition reaction with tert-butyl chloride and 2,2-dichloropropane; relative rate constants for mediated brominations; additives - Br2, BrCCl3, CH2CCl2;

triethyl(neopentyloxy)silane (18023-50-2) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With quinoline; phosphorus tribromide

methyl bromide (74-83-9) + dineopentyl phenyl phosphite (80733-03-5) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With phenol In neat (no solvent) at 20 - 33℃; for 4272h; Product distribution; Mechanism; further phosphite and halides;	50 % Chromat.

2,2-dimethylpropane (463-82-1) + 2,2-dimethyl-N-bromosuccinimide (82621-77-0) → 3,3-dimethylpyrrolidine-2,5-dione (3437-29-4) + bromodichloromethane (75-27-4) + 2,2-dimethylpropyl bromide (630-17-1) + 3-bromo-3-methylbutanoyl isocyanate (82621-87-2)

Conditions	Yield
With ethene; dichloromethane; bromine at 12℃; for 0.333333h; Irradiation; various molar ratios of educts; neopentane/methylene chloride competition with 2,2-dimethylsuccinimidyl radical; mechanism;

2,2-dimethylpropane (463-82-1) → bromodichloromethane (75-27-4) + 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With acetyl hypobromite; bromine In dichloromethane at -78℃; for 3h; Product distribution; Mechanism; Irradiation; other substrates;
With acetyl hypobromite; bromine In dichloromethane at -78℃; for 3h; Irradiation;

2,2-dimethylpropane (463-82-1) → neopentyl chloride (753-89-9) + 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With bromine; chlorine In trichlorofluoromethane at 10℃; for 0.00266667h; Irradiation; Yield given;

neopentyl tosylate (2346-07-8) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With lithium bromide In N,N,N,N,N,N-hexamethylphosphoric triamide

dineopentyl phenyl phosphite (80733-03-5) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With methyl bromide; phenol In neat (no solvent) at 20 - 33℃; for 4272h;	50 % Chromat.

2,2-Dibromo-2-(2,2-dimethyl-propoxy)-1,3-dioxa-2λ5-phospha-indan (74745-91-8) → 2-bromo-2-methylbutane (507-36-8) + 2,2-dimethylpropyl bromide (630-17-1) + 2-bromo-2-oxo-4,5-benzo-1,3,2-dioxaphospholane (3492-46-4)

Conditions	Yield
at -50℃;

bromo-neopentoxyphosphonium salt (74745-82-7) → 2,2-dimethylpropyl bromide (630-17-1)

1-oxy-2.2-dimethylpropane → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With hydrogen bromide

neopentylmercury chloride → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With water; bromine; potassium bromide

silver salt of/the/ 3,3-dimethyl-butyric acid → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
With bromine; nitrobenzene

water (7732-18-5) + bromine (7726-95-6) + chloro(2,2-dimethylpropyl)mercury (10284-47-6) + KBr → 2,2-dimethylpropyl bromide (630-17-1)

2,2-dimethylpropylamine (5813-64-9) → 2,2-dimethylpropyl bromide (630-17-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) triethylamine, 2.) glacial acetic acid / 1.) methylene chloride, 25 deg C, 8 h, 2.) 6 h, 3.) water 2: 87 percent / 200 - 220 °C / 0.3 - 0.8 Torr View Scheme

(CH3)2BrSnCH2C(CH3)3 (91734-34-8) → 2,2-dimethylpropyl bromide (630-17-1) + (CH3)Br2SnCH2C(CH3)3 (91734-43-9) + dimethyltin dibromide (2767-47-7)

Conditions	Yield
With bromine In tetrachloromethane (N2); monitored by (1)H NMR;

tert-butylmagnesium chloride (677-22-5) + 1,1-dibromomethane (74-95-3) → 1,1-dineopentylethylene (141-70-8) + 2,2,4,4-tetramethylpentane (1070-87-7) + 2,2-dimethylpropyl bromide (630-17-1) + 3-bromo-2,2,4,4-tetramethylpentane (107713-49-5)

Conditions	Yield
With 2-(CH3)-4-[1,2,2-(CH3)3-bicyclo[3.1.0]hex-3-yl]but-2-en-1-ol Further byproducts.;

2,2-dimethylpropyl bromide (630-17-1) + triphenylphosphine (603-35-0) → (2,2-dimethylpropyl)diphenylphosphine oxide (3740-04-3)

Conditions	Yield
With sodium; tert-butyl alcohol Irradiation;	100%

2,2-dimethylpropyl bromide (630-17-1) + (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate (1517-82-4) → (R)-neopentyl p-tolyl sulfoxide (21066-63-7)

Conditions	Yield
Stage #1: 2,2-dimethylpropyl bromide With potassium; potassium iodide; magnesium chloride In tetrahydrofuran for 0.333333h; Heating; Stage #2: (1R,2S,5R,SS)-(-)-menthyl p-toluenesulfinate In tetrahydrofuran for 4h; Heating; Further stages.;	99%

2,2-dimethylpropyl bromide (630-17-1) + trimethylstannyl sodium (16643-09-7) → (neopentyl)trimethylstannane (55204-72-3)

Conditions	Yield
In tetrahydrofuran 0°C in N2-atmosphere; various yields for various conditions;	99%
In tetrahydrofuran byproducts: NaBr; under argon, equimolar amounts, at 0°C; GLC;	75%

2,2-dimethylpropyl bromide (630-17-1) + 4-(4-bromo-2-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one → 4-(4-bromo-2-fluorophenyl)-1-neopentyl-1H-1,2,4-triazol-5(4H)-one

Conditions	Yield
Stage #1: 4-(4-bromo-2-fluorophenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one With potassium hydroxide In N,N-dimethyl-formamide at 20℃; for 0.166667h; Stage #2: 2,2-dimethylpropyl bromide In N,N-dimethyl-formamide at 60℃; for 12h;	99%

2,6-dichloropyridine (2402-78-0) + 2,2-dimethylpropyl bromide (630-17-1) → 2,6-di-tert-butylmethylpyridine (1140966-46-6)

Conditions	Yield
Stage #1: 2,2-dimethylpropyl bromide With magnesium In tetrahydrofuran Inert atmosphere; Stage #2: 2,6-dichloropyridine With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In tetrahydrofuran at 0℃; for 3h; Inert atmosphere; Reflux;	96%
Stage #1: 2,2-dimethylpropyl bromide With magnesium In diethyl ether at 20℃; for 1h; Reflux; Inert atmosphere; Stage #2: 2,6-dichloropyridine With 1,3-bis[(diphenylphosphino)propane]dichloronickel(II) In diethyl ether at 0℃; Reflux; Inert atmosphere;	67%

2,2-dimethylpropyl bromide (630-17-1) + cyanoaquacobinamide-c-N,N-dimethylamide → neopentylcobinamide-c-N,N-dimethylamide

Conditions	Yield
With hydrogenchloride; ammonium chloride; zinc In acetic acid Ar-atmosphere; treatment of cobalamin in 10% AcOH (contg. NH4Cl) with Zn wool for 1 h, addn. of excess neopentyl bromide (in dark), standing for 20 h; pouring into 0.001 M HCl, chromy. (Amberlite XAD-2, 10%, then 30% MeCN in 0.001 M HCl);	95%

2,2-dimethylpropyl bromide (630-17-1) + mercaptoacetic acid (68-11-1) → 2-(neopentylthio)acetic acid (1391715-39-1)

Conditions	Yield
With potassium hydroxide In ethanol for 8h; Reflux;	95%

2-(1H-pyrazol-1-yl)benzoic acid (55317-53-8) + 2,2-dimethylpropyl bromide (630-17-1) → 1-(2-neopentylphenyl)-1H-pyrazole (1189041-21-1)

Conditions	Yield
With [ruthenium(II)(η6-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]2; mesitylenecarboxylic acid; potassium carbonate In o-xylene at 120℃; for 16h; Catalytic behavior; Reagent/catalyst; Schlenk technique; Inert atmosphere; regioselective reaction;	95%

2,2-dimethylpropyl bromide (630-17-1) + (1R,2S,3R)-3-(benzylthio)camphanol → (1R,2S,3R)-3-(benzylthio)-2-neopentoxy-1,7,7-trimethylbicyclo<2.2.1>heptane

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; sodium hydride at 130℃; for 10h;	94%

2,2-dimethylpropyl bromide (630-17-1) + (1S,2R)-3,3-ethylenedioxy-1,7,7-trimethylbicyclo<2.2.1>heptan-2-ol (106708-86-5) → (1S,2R)-3,3-ethylenedioxy-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptane (106708-87-6)

Conditions	Yield
With sodium hydride 1.) N-methylpyrrolidone, 0 deg C, 1 h then r.t., 2 h; 2.) N-methylpyrrolidone, 100 deg C, 12 h then 130 deg C, 18 h;	92.3%

2,2-dimethylpropyl bromide (630-17-1) + (1R,2S,4S)-(-)-3,3-ethylenedioxy-1,7,7-trimethylbicyclo[2.2.1]heptan-2-ol (25763-72-8) → (1R,2S)-3,3-ethylenedioxy-2-(2,2-dimethylpropoxy)-1,7,7-trimethylbicyclo<2.2.1>heptane (106618-20-6)

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; sodium hydride at 130℃; for 18h;	92%
With sodium hydride 1.) N-methylpyrrolidone, 0 deg C, 1 h then r.t., 2 h; 2.) N-methylpyrrolidone, 100 deg C, 12 h then 130 deg C, 18 h;	92.1%

2,2-dimethylpropyl bromide (630-17-1) → pivalaldehyde (630-19-3)

Conditions	Yield
With dimethyl sulfoxide for 0.0358333h; Kornblum oxidation; Microwave irradiation;	91%

2,2-dimethylpropyl bromide (630-17-1) + 3,5-dimethylbenzaldehyde (5779-95-3) → C14H22O

Conditions	Yield
With magnesium In tetrahydrofuran at 20℃; Inert atmosphere;	91%

2,2-dimethylpropyl bromide (630-17-1) + N-(2-fluorophenyl)pyrimidin-2-amine (138851-61-3) → N-(2-fluoro-6-neopentylphenyl)pyrimidin-2-amine

Conditions	Yield
With (1,2-dimethoxyethane)dichloronickel(II); lithium tert-butoxide In 1,4-dioxane for 16h; Schlenk technique; Inert atmosphere;	90%
With N,N'-di-tert-butylethylenediamine; C40H32N12Ni2; lithium tert-butoxide In 1,4-dioxane at 120℃; for 16h;	77%

2,2-dimethylpropyl bromide (630-17-1) + 5-bromo-2-hydroxybenzonitrile (40530-18-5) → 5-bromo-2-(neopentyloxy)benzonitrile

Conditions	Yield
Stage #1: 5-bromo-2-hydroxybenzonitrile With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1h; Stage #2: 2,2-dimethylpropyl bromide In N,N-dimethyl-formamide at 80℃; for 3h;	90%

2,2-dimethylpropyl bromide (630-17-1) + diphenylmethyllithium (881-42-5) → 1,1-diphenyl-3,3-dimethylbutane (57123-34-9)

Conditions	Yield
In tetrahydrofuran at 25℃; for 2h;	89%

2,2-dimethylpropyl bromide (630-17-1) + 3,3-dimethyl acrylaldehyde (107-86-8) → 2,6,6-trimethyl-2-hepten-4-ol (39760-54-8)

Conditions	Yield
Stage #1: 2,2-dimethylpropyl bromide With magnesium In diethyl ether Stage #2: 3,3-dimethyl acrylaldehyde In diethyl ether at 20℃; for 3h;	88%

2,2-dimethylpropyl bromide (630-17-1) + thiophenol (108-98-5) → neopentyl phenyl sulphide (7210-80-2)

Conditions	Yield
Stage #1: thiophenol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Inert atmosphere; Stage #2: 2,2-dimethylpropyl bromide In N,N-dimethyl-formamide; mineral oil at 80℃; for 1h; Inert atmosphere;	87%
Stage #1: thiophenol With sodium ethanolate Stage #2: 2,2-dimethylpropyl bromide With Aliquat 336 In water at 70℃; for 16h; Inert atmosphere;	37%
With Aliquat 336 In water at 70℃; for 16h; Inert atmosphere;	37%

3-benzyl-1-methyl-3,7-dihydropurine-2,6-dione (63908-22-5) + 2,2-dimethylpropyl bromide (630-17-1) → 3-benzyl-7-<(2,2-dimethyl)propyl>-1-methyl xanthine (155006-66-9)

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide 1.) 1 h, 2.) reflux, 8 h;	86.6%
With sodium hydride In N,N-dimethyl-formamide 1.) 1 h, 2.) reflux, 8 h;

2,2-dimethylpropyl bromide (630-17-1) + (E)-4-methoxy-N-(1-phenylethylidene)benzenamine (2743-00-2, 125231-22-3) → 1-[2-(2,2-dimethylpropyl)phenyl]ethanone (1443686-04-1)

Conditions	Yield
Stage #1: 2,2-dimethylpropyl bromide; (E)-4-methoxy-N-(1-phenylethylidene)benzenamine With neopentylmagnesium bromide; cobalt(II) bromide; 1,3-Diisopropyl-4,5-dihydro-3H-imidazol-1-ium tetrafluoroborate In tetrahydrofuran at 0 - 20℃; for 13h; Schlenk technique; Inert atmosphere; Stage #2: With hydrogenchloride; water In tetrahydrofuran Inert atmosphere; Schlenk technique;	86%
With 1,3-diisopropylimidazolium tetrafluoroborate; neopentylmagnesium bromide; cobalt(II) bromide In tetrahydrofuran at 20℃; for 13h; Schlenk technique;	86%

2,2-dimethylpropyl bromide (630-17-1) + 4-methoxycarbonyl-1-methyl-1,4-dihydropyridine anion enolate (36907-10-5) → 1,4-dihydro-4-methoxycarbonyl-1-methyl-4-neopentylpyridine (108163-92-4)

Conditions	Yield
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide Product distribution; Rate constant; Ambient temperature; electrolysis, mercury cathode, Ag/AgI as reference electrode; substitution on some alkyl halides, single electron transfer as rate-determining step in aliphatic nucleophilic substitution;	85%
With tetra-(n-butyl)ammonium iodide In N,N-dimethyl-formamide electrolysis, reduction potential -1.20 V;	85%

2,2-dimethylpropyl bromide (630-17-1) + 1,4-bis(diphenylfluorostannyl)butane (223668-35-7) → ((C6H5)2(CH2C(CH3)3)SnCH2CH2)2 (223668-38-0)

Conditions	Yield
With Mg In tetrahydrofuran dropwise addn. of Sn-compd. to 2 equiv. of Grignard reagent (prepd. fromMg and Me3CCH2Br), refluxing for 1 d; addn. of satd. NH4Cl soln., extn. into Et2O, drying (Na2SO4), filtration, solvent removal (vac.); elem. anal.;	83%

3-iodo-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine (398117-44-7) + 2,2-dimethylpropyl bromide (630-17-1) → 1-(2,2-dimethylpropyl)-3-iodo-1H-pyrazolo[3,4-d]pyrimidine-4,6-diamine

Conditions	Yield
With caesium carbonate In N,N-dimethyl-formamide at 110℃; for 48h;	83%

2,2-dimethylpropyl bromide (630-17-1) + Natrium-diphenylarsenid (41006-64-8) → neopentyl diphenyl arsine (96503-14-9)

Conditions	Yield
In ammonia at -33℃; for 0.166667h; Irradiation;	82%

2,2-dimethylpropyl bromide (630-17-1) + trans-[1,2-bis(dimethylphosphino)ethane]2Ru(H)P(Me)Ph → methyl-(2,2-dimethylpropyl)phenylphosphine borane

Conditions	Yield
Stage #1: 2,2-dimethylpropyl bromide; trans-[1,2-bis(dimethylphosphino)ethane]2Ru(H)P(Me)Ph In tetrahydrofuran at 45℃; for 0.4h; Stage #2: With borane-THF In tetrahydrofuran at 20℃; for 1h;	82%

borane-THF (14044-65-6) + 2,2-dimethylpropyl bromide (630-17-1) + [(1,2-bis(dimethylphosphino)ethane)2RuH(methylphenylphosphine(-1H))] (882176-52-5) → methyl-(2,2-dimethylpropyl)phenylphosphine borane

Conditions	Yield
In tetrahydrofuran Ru complex reacted with neopenthyl bromide in THF for 36 h at 45°C, reacted with B compd.;	82%

Upstream product

• 186581-53-3 diazomethane 
• 507-19-7 t-butyl bromide 
• 677-22-5 tert-butylmagnesium chloride 
• 74-95-3 1,1-dibromomethane 
• 91734-34-8 (CH₃)2BrSnCH₂C(CH₃)3 
• 5813-64-9 2.2-dimethylpropylamine 
• 7732-18-5 water 
• 7726-95-6 bromine 
• 10284-47-6 chloro(2,2-dimethylpropyl)mercury 
• 74745-82-7 bromo-neopentoxyphosphonium salt 
• 74745-91-8 2,2-Dibromo-2-(2,2-dimethyl-propoxy)-1,3-dioxa-2λ⁵-phospha-indan 
• 80733-03-5 dineopentyl phenyl phosphite 
• 87444-95-9 1-(2,2-dimethyl-propyl)-2,4-diphenyl-5,6-dihydro-benzo[h]quinolinium; bromide 
• 85558-04-9 2-(2,2-Dimethyl-propoxy)-1,3-diphenyl-[1,3,2]diazaphospholidine 

Downstream Products

• 513-35-9 2-methyl-but-2-ene 
• 2987-16-8 3,3-dimethylbutyrylaldehyde 
• 60-35-5 acetamide 
• 15501-38-9 N-(1,1-dimethylpropyl)acetamide 
• 133111-34-9 1-(2,2-Dimethyl-propyl)-2-methyl-3,4-diphenyl-1H-pyrrole 
• 133111-42-9 1-(2,2-Dimethyl-propyl)-5-methyl-2,3-diphenyl-1H-pyrrole 
• 157202-48-7 2-Methyl-1,4-bis(2,2-dimethylpropyloxy)benzol 
• 623-26-7 terephthalonitrile 
• 3744-21-6 2,2-dimethyl-propyl 
• 96503-15-0 2,2-dimethyl-1-propyl phenyl selenide 
• 96532-35-3 dineopentyl selenide 
• 57123-34-9 1,1-diphenyl-3,3-dimethylbutane 
• 96503-14-9 neopentyl diphenyl arsine 
• 198-55-0 PERYLENE 

Relevant articles and documents

?- and ?-Acetoxy Radicals

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The Walling, El-Taliawi, and Zhao "Carnonyl Effect" in Radical Brominations Is an Example of HBr Reversal. It Is Not Relevant to ? and ? Radical Chemistry.

Walling, El-Taliawi, and Zhao claim that our "S? chemistry" is reproduced in photobrominations employing Br2 in the presence of carbonyl compounds (no NBS).Photobromination of alkanes by N-bromosuccinimide (NBS) shows selectivities that vary, but which show limiting values for significant ranges of rection conditions.We have attributed these different limiting values to three reaction paths which differ in involving either Br., S?, or S? as the intermediate hydrogen-abstracting radical.Walling, El-Taliawi, and Zhao (WEZ) have reported selectivities they belive are attributable to a carbonyl-bromine intermediate rather than our S?.Evidence is now presented to show that the WEZ results are due to HBr in varying amounts with or without carbonyl compounds present.This represents a fourth type of selectivity and one that is sensitive to HBr concentrations and probably arises in their systems from the following reaction: There is no carbonyl effect.This fourth type had been deliberately excluded from our work, so that reactions involving HBr reversal are not relevant to our published work on succinimidyl chemistry.Thus, the selectivities (per H basis) for the neopentane/methylene chloride competitions stand without modification, as published earlier: 0.067, 1.0 and 17 for B., S?, and S?, respectively.

Tandem cyclopropanation with dibromomethane under Grignard conditions

(Chemical Equation Presented) Tertiary Grignard reagents and dibromomethane efficiently cyclopropanate allylic (and certain homoallylic) magnesium and lithium alcoholates at ambient temperature in ether solvents. Lithium (homo)allyl alcoholates are directly cyclopropanated with magnesium and CH 2Br2 under Barbier conditions at higher temperatures. The reaction rates depend on the substitution pattern of the (homo)allylic alcoholates and on the counterion with lithium giving best results. Good to excellent syn-selectivities are obtained from α-substituted substrates, which are in accord with a staggered Houk model. In tandem reactions, cyclopropyl carbinols are obtained from allyloxylithium or -magnesium intermediates, generated in situ by alkylation of conjugated aldehydes, ketones, and esters as well as from allyl carboxylates or vinyloxiranes. Using this methodology, numerous fragrance ingredients and their precursors were efficiently converted to the corresponding cyclopropyl carbinols.

PHOTOSTIMULATED REACTIONS OF NEOPENTYL IODIDES WITH CARBANIONS IN DMSO BY THE SRN1 MECHANISM

Neopentyl iodide, 1, reacted under photostimulation with several carbanionic nucleophiles in DMSO.With acetone enolate ion only reduction and dimerization occured, but good yields of substitution products have been obtained with acetophenone, 5, and anthrone, 9, anions as nucleophiles.Nitromethane anion, 7, does not react with 1 under irradiation, but good yields of the substitution products are obtained when the photostimulated reaction is carried out in the presence of acetone enolate ions (entrainment reaction).Inhibition experiments by p-dinitrobenzene and by the radical trap TEMPO, suggest that these reactions occur by the SRN1 mechanism of nucleophilic substitution.The photostimulated reaction of 1,3-diiodo-2,2-dimethylpropane, 15, with 5 gave the disubstitution product 17 and the reduced monosubstitution product 18.It has been found that the monosubstitution product 16 (in which iodine is retained) is not an intermediate of these reactions. 1-iodoadamantane, 12, is more reactive (ca. 4.9 times) than 1 in competitive experiments toward 5 and under photostimulation.

SELECTIVE HYDROBROMINATION OF BRANCHED ALCOHOLS USING PHASE TRANSFER CATALYSIS

In the presence of quaternary ammonium phase transfer catalysts hydrobromination of branched alcohols proceed via selective SN2 mechanism practically without rearrangements.