[ CAS No. 2402-83-7 ] {[proInfo.proName]}

Name: 2402-83-7|3,3-Bis(bromomethyl)oxetane|95%
Brand: Ambeed
SKU: A115785
Price: 9.0 USD
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Quality Control of [ 2402-83-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2402-83-7 ]

Product Details of [ 2402-83-7 ]

CAS No. :	2402-83-7	MDL No. :	MFCD00269694
Formula :	C₅H₈Br₂O	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QOPMHMFIIMJWET-UHFFFAOYSA-N
M.W :	243.92	Pubchem ID :	75464
Synonyms :

Calculated chemistry of [ 2402-83-7 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	40.6
TPSA :	9.23 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.03
Log Po/w (XLOGP3) :	1.49
Log Po/w (WLOGP) :	1.79
Log Po/w (MLOGP) :	1.83
Log Po/w (SILICOS-IT) :	2.8
Consensus Log Po/w :	1.99

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.16
Solubility :	1.69 mg/ml ; 0.00693 mol/l
Class :	Soluble
Log S (Ali) :	-1.29
Solubility :	12.5 mg/ml ; 0.0511 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.268 mg/ml ; 0.0011 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.26

Safety of [ 2402-83-7 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501	UN#:	3265
Hazard Statements:	H302-H314-H319	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 2402-83-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 2402-83-7 ]
Downstream synthetic route of [ 2402-83-7 ]

[ 2402-83-7 ] Synthesis Path-Upstream 1~7

1
[ 1522-92-5 ]
[ 2402-83-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium ethanolate In ethanol at 20 - 76℃; for 3.16667 h;	(200 g, 616 mmol) and absolute EtOH (1 L). At temperature <20°C, a freshly prepared NaOEt (253 mL, 677 mmol, 21percent in EtOH) wasadded over 10 min. The reaction mixture was heated to reflux (76 °C)and a suspension was formed. After 3 h, GC analysis showed full conversionof the pentaerythritol. The reaction mixture was cooled to r.t. and the solid material was removed by filtration. The filtrate was partitionedbetween MTBE (400 mL) and H2O (550 mL). The aqueousphase was extracted with MTBE (250 mL). The combined organicphases were washed successively with H2O (250 mL) and brine (150mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was distilled with a short path distillation setup (56 °C/0.1 mbar) and130 g (85percent) of 5b was collected as an almost colorless oil.1H NMR (CDCl3, 400 MHz): δ = 4.44 (s, 4 H), 3.86 (s, 4 H).

Reference： [1] Synthesis (Germany), 2017, vol. 49, # 11, p. 2394 - 2401
[2] Journal of Organometallic Chemistry, 2007, vol. 692, # 24, p. 5395 - 5402
[3] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1939, vol. 42, p. 778[4] Chem. Zentralbl., 1940, vol. 111, # I, p. 2458
[5] Kogyo Kagaku Zasshi, 1958, vol. 61, p. 904,906[6] Chem.Abstr., 1961, p. 18696
[7] Organic Process Research and Development, 2016, vol. 20, # 3, p. 675 - 682

2
[ 115-77-5 ]
[ 2402-83-7 ]

Reference： [1] Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences, 1939, vol. 42, p. 778[2] Chem. Zentralbl., 1940, vol. 111, # I, p. 2458
[3] Chemistry of Heterocyclic Compounds, 2017, vol. 53, # 6-7, p. 811 - 821[4] Khim. Geterotsikl. Soedin., 2017, vol. 53, # 6-7, p. 811 - 821,11

3
[ 3580-97-0 ]
[ 2402-83-7 ]

Reference： [1] Journal of Organic Chemistry, 1957, vol. 22, p. 1029,1033

4
[ 1522-92-5 ]
[ 174-79-8 ]
[ 2402-83-7 ]
[ 22633-44-9 ]

Reference： [1] Environmental Science and Technology, 2005, vol. 39, # 2, p. 505 - 512

5
[ 1522-92-5 ]
[ 174-79-8 ]
[ 2402-83-7 ]
[ 22633-44-9 ]

Reference： [1] Environmental Science and Technology, 2005, vol. 39, # 2, p. 505 - 512

6
[ 2402-83-7 ]
[ 174-78-7 ]

Reference： [1] Synthesis (Germany), 2017, vol. 49, # 11, p. 2394 - 2401

7
[ 2402-83-7 ]
[ 1159599-99-1 ]

Reference： [1] Synthesis (Germany), 2017, vol. 49, # 11, p. 2394 - 2401

[ 2402-83-7 ] Synthesis Path-Downstream 1~88

1
[ 2402-83-7 ]
[ 618-32-6 ]
[ 100119-07-1 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 1029,1033

2
[ 2402-83-7 ]
[ 143-33-9 ]
[ 22030-97-3 ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1954,vol. 16,p. 3,10

3
[ 2402-83-7 ]
[ 109-89-7 ]
[ 208105-67-3 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1948,vol. 57,p. 224,228

4
[ 2402-83-7 ]
[ 75-50-3 ]
(3-bromomethyl-oxetan-3-ylmethyl)-trimethyl-ammonium; bromide [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1947,vol. 56,p. 251,255

5
[ 2402-83-7 ]
[ 75-50-3 ]
3,3-bis-trimethylammoniomethyl-oxetane; dibromide [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1947,vol. 56,p. 251,255

6
[ 2402-83-7 ]
[ 338-61-4 ]

Reference： [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1958,vol. 61,p. 904,906
Chem.Abstr.,1961,p. 18696

7
[ 2402-83-7 ]
[ 2402-82-6 ]

Reference： [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1958,vol. 61,p. 904,906
Chem.Abstr.,1961,p. 18696

8
[ 2402-83-7 ]
[ 23500-57-4 ]

Reference： [1]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1939,vol. 42,p. 778
Chemisches Zentralblatt,1940,vol. 111,p. 2458
[2]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1939,vol. 42,p. 778
Chemisches Zentralblatt,1940,vol. 111,p. 2458
[3]Patent: US2013/90328,2013,A1
[4]Patent: WO2013/53658,2013,A1

9
[ 2402-83-7 ]
[ 137530-33-7 ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1940,vol. 2,p. 3,16

10
[ 2402-83-7 ]
2,2-bis-bromomethyl-3-iodo-propan-1-ol [ No CAS ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1940,vol. 2,p. 3,16

11
[ 2402-83-7 ]
[ 120844-28-2 ]

Reference： [1]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1939,vol. 42,p. 778
    Chemisches Zentralblatt,1940,vol. 111,p. 2458
[2]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1939,vol. 42,p. 778
    Chemisches Zentralblatt,1940,vol. 111,p. 2458
[3]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1939,vol. 42,p. 778
    Chemisches Zentralblatt,1940,vol. 111,p. 2458

12
[ 1522-92-5 ]
[ 2402-83-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With sodium ethanolate; In ethanol; at 20 - 76℃; for 3.16667h;	(200 g, 616 mmol) and absolute EtOH (1 L). At temperature <20C, a freshly prepared NaOEt (253 mL, 677 mmol, 21% in EtOH) wasadded over 10 min. The reaction mixture was heated to reflux (76 C)and a suspension was formed. After 3 h, GC analysis showed full conversionof the pentaerythritol. The reaction mixture was cooled to r.t. and the solid material was removed by filtration. The filtrate was partitionedbetween MTBE (400 mL) and H2O (550 mL). The aqueousphase was extracted with MTBE (250 mL). The combined organicphases were washed successively with H2O (250 mL) and brine (150mL), dried (Na2SO4), filtered, and concentrated in vacuo. The residue was distilled with a short path distillation setup (56 C/0.1 mbar) and130 g (85%) of 5b was collected as an almost colorless oil.1H NMR (CDCl3, 400 MHz): delta = 4.44 (s, 4 H), 3.86 (s, 4 H).

Reference： [1]Synthesis,2017,vol. 49,p. 2394 - 2401
[2]Journal of Organometallic Chemistry,2007,vol. 692,p. 5395 - 5402
[3]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1939,vol. 42,p. 778
Chemisches Zentralblatt,1940,vol. 111,p. 2458
[4]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1958,vol. 61,p. 904,906
Chem.Abstr.,1961,p. 18696
[5]Organic Process Research and Development,2016,vol. 20,p. 675 - 682

13
[ 3580-97-0 ]
[ 2402-83-7 ]

Reference： [1]Journal of Organic Chemistry,1957,vol. 22,p. 1029,1033

14
[ 1522-92-5 ]
[ 174-79-8 ]
[ 2402-83-7 ]
[ 22633-44-9 ]

Reference： [1]Environmental Science and Technology,2005,vol. 39,p. 505 - 512

15
[ 2402-83-7 ]
[ 288-13-1 ]
[ 208105-64-0 ]

Reference： [1]Journal of Organometallic Chemistry,2007,vol. 692,p. 5395 - 5402

16
[ 2402-83-7 ]
[ 35842-60-5 ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1940,vol. 2,p. 3,16

17
[ 2402-83-7 ]
3-bromo-2-chloromethyl-2-iodomethyl-propan-1-ol [ No CAS ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1940,vol. 2,p. 3,16

18
[ 2402-83-7 ]
3-chloro-2,2-bis-iodomethyl-propan-1-ol [ No CAS ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1940,vol. 2,p. 3,16

19
[ 2402-83-7 ]
3-bromo-2,2-bis-iodomethyl-propan-1-ol [ No CAS ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1940,vol. 2,p. 3,16

20
[ 2402-83-7 ]
[ 19064-86-9 ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1940,vol. 2,p. 3,16

21
[ 2402-83-7 ]
1-acetoxy-3-acetylamino-2,2-bis-(acetylamino-methyl)-propane [ No CAS ]

22
[ 115-77-5 ]
[ 2402-83-7 ]

Yield	Reaction Conditions	Operation in experiment
		A 2-l Erlenmeyer flask was charged withpentaerythritol (136 g, 1 mol), 48% hydrobromic acid (680 ml,1006.4 g, 6 mol), acetic acid (100 ml, 105.1 g, 1.75 mol),and then sulfuric acid (250 ml, 458.5 g, 4.5 mol) was carefully added while stirring the reaction mixture. The obtainedsolution was refluxed for 10 h. After that, the reactionmixture was cooled to 15. The bottom (organic) layerwas separated by using a separatory funnel, and the top(aqueous) layer was extracted with chloroform (3×200 ml).The extracts were combined with the organic phase, theobtained solution was washed with water (3×75 ml). Theorganic phase was dried over anhydrous K2CO3 (20 g) forseveral hours. Then the chloroform solution wasevaporated, providing a brown liquid (275.4 g) with thefollowing composition (according to 1 NMR spectrum):3-bromo-2,2-bis(bromomethyl)propan-1-ol (3a), 3-bromo-2,2-bis(bromomethyl)propyl acetate (3b), 2,2-bis(bromomethyl)-1,3-propanediol (4a), 3-bromo-2-(bromomethyl)-2-(hydroxymethyl)propyl acetate (4b).3-Bromo-2,2-bis(bromomethyl)propan-1-ol (3a). Yield134.7 g (48.9%). 1H NMR spectrum (DMSO-d6), delta, ppm(J, Hz): 3.41 (2, d, J = 5.0, 2OH); 3.49 (6, s, CH2Br);5.26 (1H, t, J = 5.0, OH).3-Bromo-2,2-bis(bromomethyl)propyl acetate (3b).Yield 101.9 g (37.0%). 1H NMR spectrum (DMSO-d6),delta, ppm: 2.06 (3, s, OC(O)CH3); 3.57 (6, s, CH2Br); 4.06(2, s, CH2OC(O)CH3).2,2-Bis(bromomethyl)-1,3-propanediol (4a). Yield6.3 g (2.3%). 1H NMR spectrum (DMSO-d6), delta, ppm(J, Hz): 3.41 (4, d, J = 5.0, 2OH); 3.44 (4, s, CH2Br);4.84 (1H, t, J = 5.0, OH).3-Bromo-2-(bromomethyl)-2-(hydroxymethyl)propylacetate (4b). Yield 32.5 g (11.8%). 1H NMR spectrum(DMSO-d6), delta, ppm (J, Hz): 2.03 (3, s, OC(O)CH3); 3.40(2H, d, J = 4.1, CH2OH); 3.50 (4, s, CH2Br); 3.98 (2, s,CH2OC(O)CH3); 5.10 (1H, t, J = 4.6, OH). 13C NMRspectrum (CDCl3), delta, ppm: 171.22; 170.15; 63.95; 63.78;63.32; 62.33; 61.82; 44.50; 44.23; 42.67; 42.31; 34.83;34.51; 34.09; 33.53; 20.78 (for mixture 3a,b and 4a,b).The yield calculated for the target compounds 3a and 3bwas 236.6 g (69.2%). Method II. A 500-ml three-neck flask was equipped withan overhead stirrer and charged with the intermediateproducts 3a,b and 4a,b (275.4 g, 0.82 mol) from thebromination of pentaerythritol in the previous stage, andthen TBAB (4.6 g, 14 mmol) was added. The mixture wasvigorously stirred and treated with a solution of NaOH(61 g, 1.45 mol) in water (90 ml). The reaction mixture wasfurther maintained at 60 with vigorous stirring for 1 h. Afterthat, the reaction mixture was cooled, and the bottom(organic) layer was separated. The top layer was extractedwith chloroform (3×40 ml). The extracts were combinedwith the organic phase and the obtained solution waswashed with water (4×15 ml). The solvent was removed ona rotary evaporator, leaving a residue with mass of 177.1 g.The residue was separated by fractional distillation, givingthe main fraction with mass of 91.1 g. Bp 50-51 / 0.4 Torr(68-69 / 0.65 Torr56), the content of 3,3-bis(bromomethyl)oxetane (5a) was 86.5 g (95%), the yield achievedin the cyclization stage was 86.5 g (43.3%). 1H NMRspectrum (DMSO-d6), delta, ppm: 3.93 (4, s, 2Br); 4.34(4, s, CH2O).

Reference： [1]Proceedings of the Koninklijke Nederlandse Akademie van Wetenschappen, Series B: Physical Sciences,1939,vol. 42,p. 778
Chemisches Zentralblatt,1940,vol. 111,p. 2458
[2]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 811 - 821
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 811 - 821,11

23
[ 2402-83-7 ]
(3-bromomethyl-1-sulfanilyl-azetidin-3-yl)-methanol [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1949,vol. 58,p. 157,165

24
[ 2402-83-7 ]
[ 857483-86-4 ]

Reference： [1]Bulletin des Societes Chimiques Belges,1949,vol. 58,p. 157,165

25
[ 2402-83-7 ]
sulfanilic acid-(2,2-bis-chloromethyl-3-hydroxy-propylamide) [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1949,vol. 58,p. 157,165

26
[ 2402-83-7 ]
sulfanilic acid-(2-bromomethyl-2-chloromethyl-3-hydroxy-propylamide) [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1949,vol. 58,p. 157,165
[2]Bulletin des Societes Chimiques Belges,1949,vol. 58,p. 157,165

27
[ 2402-83-7 ]
sulfanilic acid-(2,2-bis-bromomethyl-3-hydroxy-propylamide) [ No CAS ]

Reference： [1]Bulletin des Societes Chimiques Belges,1949,vol. 58,p. 157,165

28
[ 2402-83-7 ]
[ 5768-16-1 ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1954,vol. 16,p. 3,10

29
[ 2402-83-7 ]
[ 5649-65-0 ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1954,vol. 16,p. 3,10

30
[ 2402-83-7 ]
[ 6246-01-1 ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1954,vol. 16,p. 3,10

31
[ 2402-83-7 ]
3,3-bis-methoxycarbonylmethyl-oxetane [ No CAS ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1954,vol. 16,p. 3,10

32
[ 2402-83-7 ]
3-bromomethyl-3-hydroxymethyl-glutaronitrile [ No CAS ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1954,vol. 16,p. 3,10

33
[ 2402-83-7 ]
4-carbamimidoyl-3-chloromethyl-3-hydroxymethyl-butyrimidic acid ethyl ester; dihydrochloride [ No CAS ]

Reference： [1]Mededelingen van de Koninklijke Vlaamse Academie voor Wetenschappen, Letteren en Schone Kunsten van Belgie, Klasse der Wetenschappen,1954,vol. 16,p. 3,10

34
[ 2402-83-7 ]
[ 111511-89-8 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium methylate; In methanol; ammonia; isopropyl alcohol;	A 9.76 g portion of <strong>[2402-83-7]3,3-bis(bromomethyl)oxetane</strong> in 30 ml of methanol was cooled in an ice bath and 13 g of dry ammonia absorbed. The reaction was sealed and the mixture stirred at room temperature for 40 hours, then evaporated to dryness. A 2.60 g portion of this residue was slurried in 10 ml of methanol and treated with a solution of 1.08 g of sodium methoxide in 15 ml of methanol. This mixture was cooled in an ice bath, stirred for 15 minutes, then evaporated to dryness. The residue was triturated with isopropanol and filtered. The filtrate was treated with 20 ml of 6N hydrochloric acid in isopropanol, stirred for 1/2 hour and the solid collected washed with isopropanol and dried, giving 1.32 g of 3,3-oxetanedimethanamine, dihydrochloride, mp 236 C. (dec.).

Reference： [1]Patent: US4880790,1989,A

Yield	Reaction Conditions	Operation in experiment
		Preparation of Additive D: STR6 A quantity of 3-bromo-2,2-bis(bromomethyl)-1-propanol is treated with base to form 3,3-bis(bromomethyl)oxetane which is then reacted, with stirring, at room temperature for 30 hours, with a stoichiometric amount of potassium 2,4,6-tribromophenate dissolved in dimethyl formamide. The reaction product formed, 3,3-bis[(2,4,6-tribromophenoxy)methyl]oxetane, is recovered by pouring the reaction mixture into a quantity of distilled water and extracting the resulting mixture twice with methylene chloride.

36
(C₄H₉)3SnOCH₂C(CH₂Br)3 [ No CAS ]
[ 2402-83-7 ]
[ 1461-23-0 ]

Reference： [1]Journal of Organometallic Chemistry,1973,vol. 47,p. 337 - 350
[2]Gmelin Handbuch der Anorganischen Chemie,Gmelin Handbook: Sn: Org.Comp.12, 1.4.1.1.1.5.2.1.7, page 69 - 97

37
[ 2402-83-7 ]
[ 402-46-0 ]
2-(4-fluoro-benzenesulfonyl)-2-aza-spiro[3.3]heptane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		Preparation of 2-(4-fluoro-benzenesulfonyl)-2-aza-spiro[3.3]heptane To a cooled (ice-water bath) solution of 4-fluoro-benzenesulfonamide (320 mg, 1.83 mmol) in N,N-dimethylformamide (5 mL), was added sodium hydride (150 mg, 60% dispersion, 3.75 mmol) portion-wise. After the mixture was stirred at 0 C. for 10 minutes, a solution of 3,3-bis-bromomethyl-oxetane (440 mg, 1.8 mmol) in N,N-dimethylformamide (3 mL) was added. The resulting mixture was stirred at room temperature overnight, then neutralized with 1 N hydrochloric acid, and extracted with ethyl acetate (20 mL3). The combined organic layers were washed with brine (20 mL3), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography (elution with 20% ethyl acetate in petroleum ether) to afford 2-(4-fluoro-benzenesulfonyl)-2-aza-spiro[3.3]heptane (120 mg, 26%) as a white solid (reference: Blizzard T. A. et al., Bioorg. Med. Chem. Lett. 14 (2004) 3861-3864), MS cald, for C12H14FNO2S 255, obsd. (ESI+) [(M+H)+] 256.

Reference： [1]Patent: US2010/125058,2010,A1 .Location in patent: Page/Page column 31

38
[ 2402-83-7 ]
[ 93169-36-9 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonia; In ethanol; at 50℃; under 4560.31 Torr;	EXAMPLE 4; (5-{2-r6-(2-Chloro-5-fluorophenyl)-2,6-diazaspiro[3.31hept-2-yll-l ,3-thiazol-5-yll-2H-tetrazol-2-yI)acetic acid; Step 1 : Oxetane-3 ,3-diyldimethanamine dihydrobromide; Into a 5 L pressure tank reactor was placed <strong>[2402-83-7]3,3-bis(bromomethyl)oxetane</strong> (350 g, 1.43 mol). To this was added ethanol (3.2 L), followed by addition of ammonia gas. The resulting solution was stirred overnight. The reaction temperature was maintained at 50 0C with a pressure of ammonia gas of 6 atmospheres. The mixture was concentrated under reduced10 pressure to give the title compound as a beige solid. 1H NMR (400 MHz, D2O): delta 4.59 (4H, s), 3.41 (4H, s).

Reference： [1]Patent: WO2010/108268,2010,A1 .Location in patent: Page/Page column 67-68

39
[ 2402-83-7 ]
[ 141-43-5 ]
[ 26096-35-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethanol; for 72h;Reflux;	) 2-(2-Oxa-6-aza-spiror3.31hept-6-vn-ethanol (GB 1 169 027)3,3-Bis-bromomethyl-oxetane (Journal of Organometallic Chemistry, 2007 , 692/24 5395- 5402, 75.31 g (308.7 mmol)) , 28,28 g (463 mMol) ethanolamine and 127.82 g K2C03 were refluxed in ethanol (800 mL) for 72 hours. The reaction mixture was cooled and filtered and the filtrate was concetrated in vacuo. The residue was destilled to yield 46.40 g of title compound as an oil (bp.: 74-80 C at 0.02 mbar) GC-HRMS 143.1 .

Reference： [1]Patent: WO2012/153154,2012,A1 .Location in patent: Page/Page column 35

40
[ 2402-83-7 ]
[ 1408284-88-7 ]

Reference： [1]Patent: WO2012/153154,2012,A1

41
[ 2402-83-7 ]
[ 1408284-85-4 ]

Reference： [1]Patent: WO2012/153154,2012,A1

42
[ 2402-83-7 ]
[ 1408284-90-1 ]

Reference： [1]Patent: WO2012/153154,2012,A1

43
[ 2402-83-7 ]
[ 1408284-95-6 ]

Reference： [1]Patent: WO2012/153154,2012,A1

44
[ 2402-83-7 ]
[ 1408284-94-5 ]

Reference： [1]Patent: WO2012/153154,2012,A1

45
[ 2402-83-7 ]
[ 1408284-57-0 ]

Reference： [1]Patent: WO2012/153154,2012,A1

46
[ 2402-83-7 ]
[ 1408284-62-7 ]

Reference： [1]Patent: WO2012/153154,2012,A1

47
[ 2402-83-7 ]
[ 1408284-70-7 ]

Reference： [1]Patent: WO2012/153154,2012,A1

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[ 2402-83-7 ]
6-(4-fluoro-phenyl)-3-{3-methoxy-4-[2-(2-oxa-6-aza-spiro[3.3]hept-6-yl)-ethoxy]-phenyl}-3H-thieno[3,2-d]pyrimidin-4-one maleate [ No CAS ]

Reference： [1]Patent: WO2012/153154,2012,A1

49
[ 2402-83-7 ]
[ 17607-20-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium azide; tetrabutylammomium bromide; In water; for 2h;Heating;	A 500-ml Erlenmeyer flask was chargedwith a solution of NaN3 (65 g, 1 mol) and TBAB (3.22 g,10 mmol) in water (120 ml). The solution was vigorouslystirred on a magnetic stirrer (1000 rpm), and compound 5a(91.1 g, 0.355 mol) was added. While continuing thevigorous stirring, the obtained biphasic reaction mixturewas refluxed for 2 h. The reaction flask was then cooled toroom temperature and the reaction mixture was extractedwith benzene (3×100 ml). The extracts were combined andthe obtained solution was washed with water (4×40 ml).The benzene solution was dried over anhydrous MgSO4.The solvent was then evaporated, the mass of residue was54.88 g, content of 3,3-bis(azidomethyl)oxetane (5b)was higher than 98%, the yield of azidation stage was92.1%.The overall yield of BAMO (5b) for all stages startingfrom pentaerythritol was 46.4 g (27.6%). The product wasa light-yellow liquid. Bp 80-84 / 0.4 Torr (79-81 /0.4 Torr57). IR spectrum (thin film), nu, cm-1: 2100 (-N3), 997(C-O- in cyclic ethers). 1H NMR spectrum (DMSO-d6),delta, ppm: 3.72 (4, s, CH2N3); 4.32 (4, s, CH2O). 13C NMRspectrum (CDCl3), delta, ppm: 43.42 (s, N3CH2CCH2N3);54.15 (s, CH2N3); 76.41 (s, CH2O). Found, %: C 35.73;H 4.82; N 50.04. C5H8N6O. Calculated, %: C 35.71;H 4.80; N 49.98.
	With sodium azide; tetrabutylammomium bromide; In water; at 70℃;	A mixture of <strong>[2402-83-7]3,3-bis(bromomethyl)oxetane</strong> (25 g, 100 mmol) and sodium azide (14.3 g, 220 mmol) in water (65 ml) was added tetrabutylazanium bromide (1.61 g, 5 mmol). The reaction mixture was heated with stirring at 70 C. overnight. The reaction mixture was cooled to room temperature and extracted with dichloromethane (50 mL*3). The combined organic layers were washed with water, dried over sodium sulphate and concentrated in vacuo to afford 18.7 g of 3,3-bis-azidomethyl-oxetane as light yellow oil. The crude product was used for next step without further purification.
	With sodium azide; tetrabutylammomium bromide; In water; at 70℃;	Step 1. Preparation of 3,3-Bis-azidomethyl-oxetane A mixture of <strong>[2402-83-7]3,3-bis(bromomethyl)oxetane</strong> (25 g, 100 mmol) and sodium azide (14.3 g, 220 mmol) in water (65 ml) was added tetrabutylazanium bromide (1.61 g, 5 mmol). The reaction mixture was heated with stirring at 70 C overnight. The reaction mixture was cooled to room temperature and extracted with dichloromethane (50 mL x 3). The combined organic layers were washed with water, dried over sodium sulphate and concentrated in vacuo to afford 18.7 g of 3,3- bis-azidomethyl-oxetane as light yellow oil. The crude product was used for next step without further purification.

Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 811 - 821
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 811 - 821,11
[2]Patent: US2013/90328,2013,A1 .Location in patent: Paragraph 0138; 0139
[3]Patent: WO2013/53658,2013,A1 .Location in patent: Page/Page column 21-22

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benzyl 5-(4-methoxybenzyl)-3,6-dioxo-1,2,3,4,5,6,7,8-octahydropyrazolo[4,3-c]azepin-7-ylcarbamate [ No CAS ]
benzyl (10'-(4-methoxybenzyl)-9'-oxo-8',9',10',11'-tetrahydro-2'H,4'H,7'H-spiro[oxetane-3,3'-[1,3]oxazino[3',2':1,5]pyrazolo[4,3-c]azepin]-8'-yl)carbamate [ No CAS ]

Reference： [1]European Journal of Organic Chemistry,2015,vol. 2015,p. 3572 - 3576

51
[ 2402-83-7 ]
[ 100-46-9 ]
[ 46246-91-7 ]

Yield	Reaction Conditions	Operation in experiment
70%	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 60℃; for 18h;	In a 2 L reaction flask, bis(bromomethyl)oxetane (5b; 129 g, 518mmol) was dissolved in anhyd DMF (1300 mL). At r.t., benzylamine(61.1 g, 570 mmol) and DBU (166 g, 1088 mmol) were added. The reaction mixture was stirred for 18 h at 60 C at which point, GC analysisshowed clean conversion into 6. The reaction mixture was poured into a stirring mixture of MTBE/EtOAc (1 L:1 L) and brine/H2O (1 L:0.5L). The aqueous phase was extracted twice with MTBE/EtOAc (1:1,800 mL and 400 mL) and with EtOAc (2 × 250 mL). The combined organic phases were washed with brine, dried (Na2SO4), filtered, and concentrated in vacuo. The residue was purified by a short-path distillation (96 C/0.02 mbar) providing 69 g (70%) of 6 as a colorless oil. 1H NMR (CDCl3, 400 MHz): delta = 7.33-7.22 (m, 5 H), 4.74 (s, 4 H), 3.54(s, 2 H), 3.36 (s, 4 H).13C NMR (DMSO-d6, 100 MHz): delta = 138.3 (C), 128.2 (CH), 128.1 (CH),126.8 (CH), 80.0 (CH2), 62.9 (CH2), 62.5 (CH2), 38.5 (C).MS (EI, 70 eV): m/z (%) = 91.1 (100, [Bn]+·), 188 (10, [M - 1]+·), 189 (7,[M]+·).

Reference： [1]Synthesis,2017,vol. 49,p. 2394 - 2401
[2]Organic Process Research and Development,2016,vol. 20,p. 675 - 682

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[ 2402-83-7 ]
(trans)-N₁-(6-methylquinazolin-4-yl)cyclohexane-1,4-diamine bis-hydrochloride [ No CAS ]
N-((trans)-4-(2-oxa-6-azaspiro[3,3]heptan-6-yl)cyclohexyl)-6-methylquinazolin-4-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		<strong>[2402-83-7]3,3-Bis(bromomethyl)oxetane</strong> (18.52 mg, 0.076 mmol), (trans)-N1-(6-methylquinazolin-4-yl)cyclohexane-1,4-diamine bis-hydrocloride (25 mg, 0.076 mmol), potassium carbonate (31.5 mg, 0.228 mmol), and acetonitrile (1500 tl) were added to a vial. The vial was sealed and its contents were stirred for 2 hours at 80 C. Dissolution was never fully achieved, so DMF (500 .il) and DBU (25 .il, 0.166 mmol) were added. The vial was sealed and its contents were stirred overnight at 80 C. The residue was filtered and purified by masstriggered reverse phase HPLC (ACN/water with 0.1% NH4OH modifier). The purified fractions were lyophilized via reduced pressure to afford the title compound. MS: 339 (M+1). ?H NMR (600 MHz, DMSO-d6) oe 8.33 (s, 1H), 8.05 (s, 1H), 7.70 (d, J= 7.7 Hz, 1H), 7.54-7.50 (m, 2H), 4.55 (s, 4H), 4.10-4.01 (m, 1H), 3.20 (s, 4H), 2.41 (s, 3H), 1.89 (d, J=13.2 Hz, 2H), 1.85-1.83 (m, 1H), 1.71 (d, J= 12.2, 2H), 1.34 (q, J= 12.5 Hz, 2H); 0.95 (q, J=12.2Hz,2H).

Reference： [1]Patent: WO2016/53769,2016,A1 .Location in patent: Page/Page column 56; 57

53
[ 2402-83-7 ]
[ 174-78-7 ]