637-97-8

Basic information

• Product Name: SEC-AMYL IODIDE
• Synonyms: 2-IODOPENTANE;SEC-AMYL IODIDE;2-iodo-pentan;Pentane,2-iodo-;Pentane,2-iodo(DL);Pentane,2-iodo-,(±)-;s-Amyliodide;1-Methylbutyl iodide
• CAS NO: 637-97-8
• Molecular Formula: C₅H₁₁I
• Molecular Weight: 198.05
• EINECS: 211-311-8
• Mol File: 637-97-8.mol
• Article Data: 10

Chemical Properties

• Melting Point: -85.6°C (estimate)
• Boiling Point: 154.22°C (estimate)
• Flash Point: 44.6 °C
• Appearance: /
• Density: 1.5024
• Vapor Pressure: 5.82mmHg at 25°C
• Refractive Index: 1.4934
• Solubility: Chloroform
• CAS DataBase Reference: SEC-AMYL IODIDE(CAS DataBase Reference)
• NIST Chemistry Reference: SEC-AMYL IODIDE(637-97-8)
• EPA Substance Registry System: SEC-AMYL IODIDE(637-97-8)

Safety Data

• Hazardous Substances Data: 637-97-8(Hazardous Substances Data)

Usage

Uses

2-Iodopentane is used as a reagent to alkylate methyl cyanoacetate in the synthesis of Thiopental (T344800), a drug that is required for the induction of anasthesia.

InChI:InChI=1/C5H11I/c1-3-4-5(2)6/h5H,3-4H2,1-2H3/t5-/m0/s1

Synthetic route

2-bromopentane (107-81-3) → 2-iodopentane (637-97-8)

Conditions	Yield
With iodide; <p>-(CH2)3-<sup>+</sup>NBu3</p> In water at 110℃; for 5.5h;	38%
With I*2H2O In toluene at 90℃; Rate constant;

(+/-)-2-pentanol (6032-29-7) → 2-iodopentane (637-97-8)

Conditions	Yield
With 1H-imidazole; iodine; triphenylphosphine In dichloromethane at 0℃; for 2h;	32%
(i) P2I4, CS2, (ii) K2CO3; Multistep reaction;
With iodine; triphenylphosphine In N,N-dimethyl-formamide
Multi-step reaction with 2 steps 1: pyridine 2: NaI View Scheme
Multi-step reaction with 2 steps 1: PCl3 2: HI View Scheme

(S)-2-pentanol (26184-62-3) → 2-iodopentane (637-97-8) + 3-pentyl iodide (1809-05-8)

Conditions	Yield
With phosphorus; iodine

1-penten (109-67-1) → 2-iodopentane (637-97-8)

Conditions	Yield
With hydrogen iodide
With water; hydrogen iodide

2-pentyl tosylate (3813-69-2) → 2-iodopentane (637-97-8)

Conditions	Yield
With acetone; sodium iodide

acetylacetone (123-54-6) → 2-iodopentane (637-97-8)

Conditions	Yield
With hydrogen iodide at 100℃;

phosphonic acid bis-(1-methyl-butyl) ester (1809-16-1) → 2-iodopentane (637-97-8)

Conditions	Yield
With hydrogen iodide

phosphorous acid tris-(1-methyl-butyl) ester (20329-32-2, 30356-02-6) → 2-iodopentane (637-97-8)

Conditions	Yield
With hydrogen iodide

diphenyl sec-pentyloxyphosphine (38011-61-9) → 2-iodopentane (637-97-8)

Conditions	Yield
With hydrogen iodide

pentane (109-66-0) → 2-iodopentane (637-97-8) + 3-pentyl iodide (1809-05-8)

Conditions	Yield
With sodium hydroxide; iodoform at 25℃; for 24h; Iodination; Title compound not separated from byproducts;
With CCl4*2AlI3 In dichloromethane at -20℃; for 1.5h;
With sodium azide; dihydrogen peroxide; iodine; acetic anhydride In water at 0 - 40℃; for 13h; Title compound not separated from byproducts;
With sodium periodate; sodium azide; potassium iodide In acetic acid at 25℃; for 9h;

hydrogen iodide (10034-85-2) + acetylacetone (123-54-6) → 2-iodopentane (637-97-8)

Conditions	Yield
at 100 - 105℃;

hydrogen iodide (10034-85-2) + 2-pentene (109-68-2) → 2-iodopentane (637-97-8)

(S)-2-pentanol (26184-62-3) + hydrogen iodide (10034-85-2) → 2-iodopentane (637-97-8)

Conditions	Yield
at 100℃;

1-penten (109-67-1) + hydrogen iodide (10034-85-2) → 2-iodopentane (637-97-8)

methyl-cyclobutane (598-61-8) + hydrogen iodide (10034-85-2) → 2-iodopentane (637-97-8)

1-penten (109-67-1) + water (7732-18-5) + hydrogen iodide (10034-85-2) → 2-iodopentane (637-97-8)

d-methylpropylcarbinol → 2-iodopentane (637-97-8)

Conditions	Yield
With hydrogen iodide at 100℃; levorotatory 2-iodo-pentane;

methyl-n-propylcarbinol → 2-iodopentane (637-97-8)

Conditions	Yield
With phosphorus; iodine

(+/-)-2-pentanol (6032-29-7) + iodine (7553-56-2) + phosphorus → 2-iodopentane (637-97-8) + 3-pentyl iodide (1809-05-8)

1-penten (109-67-1) + hydrogen iodide (10034-85-2) → 2-iodopentane (637-97-8) + amyl iodide (628-17-1)

Conditions	Yield
ohne Loesungsmittel;

pentan-2-yl methane sulfonate (101944-72-3) → 2-iodopentane (637-97-8)

Conditions	Yield
With sodium iodide

pentane (109-66-0) → 2-iodopentane (637-97-8) + 3-pentyl iodide (1809-05-8) + amyl iodide (628-17-1)

Conditions	Yield
With bromine; iodine; sodium t-butanolate at 40℃; Title compound not separated from byproducts;
With iodine; sodium t-butanolate at 40℃; Title compound not separated from byproducts;
With bromine; iodine; sodium t-butanolate In cyclohexane Product distribution; Further Variations:; Reagents;

2-iodopentane (637-97-8) → 4-methyloctane (2216-34-4)

Conditions	Yield
With Li2[di-n-butylcyanocuprate] In tetrahydrofuran at -50℃; for 2h;	99%

2-iodopentane (637-97-8) + MC70 (1031367-64-2) → (R,S)-6,7-dimethoxy-2-((4’-(2-pentoxy)biphen-4-yl)methyl)-1,2,3,4-tetrahydroisoquinoline

Conditions	Yield
With potassium carbonate In acetonitrile for 18h; Reflux;	65%

piperidin-4-one (41661-47-6) + 2-iodopentane (637-97-8) → 1-(pentan-2-yl)piperidin-4-one

Conditions	Yield
With potassium carbonate In acetonitrile at 80℃; for 16h;	48%

2-iodopentane (637-97-8) + hydroperoxytriisopropylsilane → triisopropyl(pentan-2-ylperoxy)silane

Conditions	Yield
With silver(l) oxide In pentane at 20℃; for 16h;	47%

2-iodopentane (637-97-8) + phenylacetonitrile (140-29-4) → (1-Methylbutyl)phenylacetonitril (26887-10-5)

Conditions	Yield
With sodium amide In toluene; benzene at 80℃; for 1h;	41%

2-iodopentane (637-97-8) + 3-methoxyl-N-(quinolin-8-yl)benzamide (341020-03-9) → C22H24N2O2

Conditions	Yield
With diphenyl hydrogen phosphate; oxygen; palladium diacetate; sodium hydrogencarbonate In tert-Amyl alcohol; para-xylene at 130℃; for 24h; Sealed tube;	31%

2-iodopentane (637-97-8) + potassium ethoxide (917-58-8) → (E)-pent-2-ene (646-04-8)

2-iodopentane (637-97-8) + sodium diethylmalonate (996-82-7) → diethyl (1-methylbutyl)malonate (117-47-5)

2-iodopentane (637-97-8) + sodium thiomethoxide (5188-07-8) → 1-methylbutyl methyl sulfide (13286-91-4)

Conditions	Yield
With ethanol

2-iodopentane (637-97-8) + silver(I) acetate (563-63-3) → 2-Pentyl acetate (626-38-0)

2-iodopentane (637-97-8) + sodium ethyl acetylacetate enolate (1007476-32-5) → 2-(1-methyl-butyl)-acetoacetic acid ethyl ester (23550-23-4)

Conditions	Yield
With benzene

2-iodopentane (637-97-8) → (E)-pent-2-ene (646-04-8)

Conditions	Yield
With potassium ethoxide at 80℃;

2-iodopentane (637-97-8) → (+/-)-2-pentanol (6032-29-7)

Conditions	Yield
With lead(II) hydroxide on calcium carbonate
With silver(I) acetate Verseifung des entstandenen Acetats durch Kali;

2-iodopentane (637-97-8) → 2-pentyl fluoride (590-87-4)

Conditions	Yield
With silver fluoride

2-iodopentane (637-97-8) + ethyl diethyl malonate (133-13-1) → diethyl ethyl(1-methyl-butyl)malonate (76-72-2)

Conditions	Yield
With sodium; toluene

2-iodopentane (637-97-8) + trimethylamine (75-50-3) → trimethyl-(1-methyl-butyl)-ammonium; iodide (16892-55-0)

Conditions	Yield
With acetonitrile
In methanol Ambient temperature;

2,4,4-trimethyl oxazoline (1772-43-6) + 2-iodopentane (637-97-8) → 4,4-dimethyl-2-(2-methyl-pentyl)-4,5-dihydro-oxazole

Conditions	Yield
(i) LDA, THF, (ii) /BRN= 1718832/; Multistep reaction;

(4S,5S)-(-)-4,5-dihydro-4-methoxymethyl-2-methyl-5-phenyloxazole (52075-14-6) + 2-iodopentane (637-97-8) → 4-methoxymethyl-2-(2-methyl-pentyl)-5-phenyl-4,5-dihydro-oxazole (52230-94-1)

Conditions	Yield
With lithium diisopropyl amide In tetrahydrofuran

2-iodopentane (637-97-8) + 1-dimethylamino-non-1-en-3-one (63859-48-3) → 4-methyl-tridec-5t-en-7-one

Conditions	Yield
With magnesium In diethyl ether

C6H4NCH2CHCCH2 (491-35-0) + 2-iodopentane (637-97-8) → 4-methyl-2-(pentan-2-yl)quinoline (93845-95-5)

Conditions	Yield
With acetic acid ; ferriacetate; trifluoroacetic acid; dibenzoyl peroxide In acetonitrile for 4h; Heating;	97 % Turnov.

acridine (260-94-6) + 2-iodopentane (637-97-8) → N-2-Pentylacridiniumiodid

Conditions	Yield
In xylene for 3h; Heating;

Upstream product

• 109-67-1 1-penten 
• 107-81-3 2-bromopentane 
• 6032-29-7 (+/-)-2-pentanol 
• 7553-56-2 iodine 
• 101944-72-3 pentan-2-yl methane sulfonate 
• 109-66-0 pentane 
• 10034-85-2 hydrogen iodide 
• 7732-18-5 water 
• 598-61-8 methyl-cyclobutane 
• 26184-62-3 (S)-2-pentanol 
• 109-68-2 2-pentene 
• 123-54-6 acetylacetone 
• 38011-61-9 diphenyl sec-pentyloxyphosphine 
• 20329-32-2 phosphorous acid tris-(1-methyl-butyl) ester 

Downstream Products

• 646-04-8 (E)-pent-2-ene 
• 117-47-5 diethyl (1-methylbutyl)malonate 
• 626-38-0 2-Pentyl acetate 
• 6032-29-7 (+/-)-2-pentanol 
• 2216-34-4 4-methyloctane 
• 109-67-1 1-penten 
• 109-66-0 pentane 
• 109-68-2 2-pentene 
• 591-50-4 iodobenzene 
• 93845-95-5 4-methyl-2-(pentan-2-yl)quinolone 
• 65-85-0 benzoic acid 
• 103191-32-8 IrClI(CH(CH₃)CH₂CH₃)(CO)(P(CH₃)2C₆H₅)2 

Relevant articles and documents

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